Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production

ABSTRACT

The dihalopropene compounds of the general formula [I ] have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.

This application is a divisional of Application Ser. No. 08/809,865,filed on May 20, 1997 now U.S. Pat. No. 5,922,880. Application Ser. No.08/809,865 is the national phase of PCT International Application No.PCT/JP95/02080 filed on Oct. 12, 1995 under 35 U.S.C. § 371. The entirecontents of each of the above identified applications are herebyincorporated by reference.

TECHNICAL FIELD

The present invention relates to dihalopropene compounds,insecticidal/acaricidal agents containing these compounds as activeingredients, and intermediates for their production.

BACKGROUND ART

As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/1974, for example,it is well known that some kinds of propene compounds can be used as anactive ingredient of insecticides.

In view of their insecticidal/acaricidal activity, it cannot always besaid that these compounds are satisfactorily effective for the controlof noxious insects, mites and ticks.

DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound havingexcellent insecticidal/acaricidal activity. As a result, they have foundthat particular dihalopropene compounds have satisfactoryinsecticidal/acaricidal activity for the control of noxious insects,mites and ticks, thereby completing the present invention.

That is, the present invention provides a dihalopropene compound(hereinafter referred to as the present compound) of the generalformula: ##STR1## wherein Z is oxygen, sulfur or NR⁴ (wherein R⁴ ishydrogen or C₁ -C₃ alkyl); Y is oxygen, sulfur or NH; X's areindependently chlorine or bromine; R², R³ and R¹⁰ are independentlyhalogen, C₁ -C₃ haloalkyl or C₁ -C₃ alkyl; t is an integer of 0 to 2;and R is Q₁, Q₂, Q₃, Q₄, Q₅, Q₆ or Q₇ of the general formula: ##STR2##wherein A is an optionally substituted heterocyclic ring group, providedthat when A is an optionally substituted heterocyclic ring groupcontaining two oxygen atoms and a condensed benzene ring, A isoptionally substituted 1,3-benzodioxolan-2-yl or optionally substituted1,4-benzodioxan-2-yl; B is oxygen, S(O)_(q), NR⁹, C(=G¹)G² or G¹ C(=G²);q is an integer of 0 to 2; R⁹ is hydrogen, acetyl or C₁ -C₃ alkyl; G¹and G² are independently oxygen or sulfur; R⁵, R⁶, R⁷, R¹¹ and R¹² areindependently hydrogen, C₁ -C₃ alkyl or trifluoromethyl; R¹³ and R¹⁴ areindependently hydrogen, C₁ -C₃ alkyl, trifluoromethyl or halogen; p isan integer of 0 to 6; and s is an integer of 1 to 6.

The present invention further provides an insecticidal/acaricidal agentcontaining the above dihalopropene compound as an active ingredient.

The present invention further provides the following compounds which areuseful as intermediates for producing some of the present compounds:

a phenol compound which is3,5-dichloro-4-(2-(2-(4-chlorophenyl)-1,3dioxolan-4-yl)ethoxy)phenol;

compounds of the general formula: ##STR3## wherein R⁵, R⁶ and R⁷ areindependently hydrogen, C₁ -C₃ alkyl or trifluoromethyl; R¹⁵ is halogen,C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; R²,R³ and R¹⁰ are independently halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl;t is an integer of 0 to 2; u is an integer of 1 to 4; w is an integer of1 to 4; and B¹ is oxygen, S(O)_(q) or NR⁹ wherein R⁹ is hydrogen, acetylor C₁ -C₃ alkyl and q is an integer of 0 to 2;

compounds of the general formula [I ] wherein R⁵, R⁶ and R⁷ are allhydrogen; and R² and R³ are independently halogen or C₁ -C₃ alkyl; and

2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine.

DETAILED DESCRIPTION OF THE INVENTION

The variables in the above formulae for the present compounds and theirintermediates can take the following specific examples.

Examples of the C₁ -C₃ alkyl group represented by R², R³, R⁴, R⁵, R⁶,R⁷, R⁹, R¹⁰, R¹¹ , R¹², R¹³ or R¹⁴ are methyl, ethyl, n-propyl andisopropyl.

Examples of the halogen atom represented by R¹³ or R¹⁴ are fluorine,chlorine, bromine and iodine.

Examples of the heterocyclic ring in the optionally substitutedheterocyclic ring group represented by A are isoxazole, isothiazole,thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole,imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4tetrazole, pyridine,pyridaiine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine,indole, benzofuran, thianaphthalene, indazole, benzimidazole,benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline,isoquinoline, quinoxaline, quinazole, piperidine, piperazine,tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane,dioxolane and benzodioxolane.

Examples of the substituent on the optionally substituted heterocyclicring group represented by A are those of the general formula: (R⁸)_(r)(wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁-C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio,C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂ haloalkylsulfinyl, C₁-C₂ haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino, acetamido, acetyl,haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁-C₂ alkyl)aminocarbonyl or [di(C₁ -C₂ alkyl)amino]carbonyl, or R⁸ isphenyl, benzyl, phenoxy, benzyloxy or pyridyloxy, each of which isoptionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁-C₄ alkoxy or C₁ -C₃ haloalkoxy; and r is an integer of 0 to 7.

Examples of the halogen atom represented by R⁸ or present in R⁸ arefluorine, chlorine, bromine and iodine.

Examples of the C₁ -C₄ alkyl group represented by R⁸ or present in R⁸are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl andtert-butyl.

Examples of the C₁ -C₃ haloalkyl group represented by R⁸ or present inR⁸ are trifluoromethyl, difluoromethyl, bromodifluoromethyl,2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 2,2,3,3,3-pentafluoropropyl, 3,3,3-trifluoropropyl, 1-fluoropropyl,2-chloropropyl and 3-bromopropyl.

Examples of the C₁ -C₄ alkoxy group represented by R⁸ or present in R⁸are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,isobutoxy and tert-butoxy.

Examples of the C₁ -C₃ haloalkoxy group represented by R⁸ or present inR⁸ are trifluoromethoxy, difluoromethoxy, bromofluoromethoxy,2-fluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-chloro-1,1,2-trifluoroethoxy, 2-bromo1,1,2-trifluoroethoxy,1,1,2,2-tetrafluoroethoxy, 1,2,2,3,3,3-hexafluoropropoxy,3-fluoropropoxy, 3-chloropropoxy, 3-bromopropoxy,2,2,3,3,3-pentafluoropropoxy, 3,3,3-trifluoropropoxy and1,1,2,2,2-pentafluoroethoxy.

Examples of the C₁ -C₃ alkylthio group represented by R⁸ are methylthio,ethylthio, n-propylthio and isopropylthio.

Examples of the C₁ -C₃ haloalkylthio group represented by R⁸ aretrifluoromethylthio, difluoromethylthio, bromodifluoromethylthio,2,2,2-trifluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio,2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio,2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio,3-fluoropropylthio, 3-chloropropylthio, (3-bromopropyl)thio,2,2,3,3,3-pentafluoropropylthio and 3,3,3-trifluoropropylthio.

Examples of the C₁ -C₂ alkylsulfinyl group represented by R⁸ aremethylsulfinyl and ethylsulfinyl.

Examples of the C₁ -C₂ alkylsulfonyl group represented by R⁸ aremethylsulfonyl and ethylsulfonyl.

Examples of the C₁ -C₂ haloalkylsulfinyl group represented by R⁸ aretrifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl andperfluoroethylsulfinyl.

Examples of the C₁ -C₂ haloalkylsulfonyl group represented by R⁸ aretrifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl andperfluoroethylsulfonyl.

Examples of the C₂ -C₄ alkenyl group represented by R⁸ are vinyl,isopropenyl, 1-propenyl, 2-ethyl-1-propenyl, 1-methyl-1-propenyl, allyl,2-methylpropenyl and 2-butenyl.

Examples of the C₂ -C₄ haloalkenyl group represented by R⁸ are2,2-dichloroethenyl, 2,2-dibromoethenyl, 3,3-dichloroallyl,3,3-dibromoallyl, 2,3-dichloroallyl, 2,3-dibromoallyl,2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl and3-chloro-2-butenyl.

Examples of the C₂ -C₄ alkynyl group represented by R⁸ are ethynyl,1-propynyl, 2-propynyl and 1-methyl-2-propynyl.

Examples of the C₂ -C₄ haloalkynyl group represented by R⁸ arechloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl,3-bromo-2-propynyl, 3-iodo-2-propynyl, 1-methyl-3-chloro-2-propynyl,1-methyl-3-bromo-2-propynyl and 1-methyl-3-iodo-2-propynyl.

Examples of the haloacetyl group represented by R⁸ aretrifluoromethylacetyl and trichloroacetyl.

Examples of the C₃ -C₆ cycloalkyl group represented by R⁸ arecyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Examples of the C₅ -C₆ cycloalkenyl are 1-cyclopentenyl,2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl and3-cyclohexenyl.

Examples of the (C₁ -C₂ alkyl)aminocarbonyl group represented by R⁸ aremethylaminocarbonyl and ethylamino carbonyl.

Examples of the [di(C₁ -C₂ alkyl)amino]carbonyl group represented by R⁸are dimethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl anddiethylaminocarbonyl.

The following are preferred examples of the present compound:

dihalopropene compounds wherein A is a 5- or 6-membered heterocyclicring group containing at least one oxygen, sulfur or nitrogen andoptionally substituted by (R⁸)_(r) (wherein R⁸ is halogen, nitro, cyano,C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃alkylthio, C₁ -C₃ haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂alkylsulfonyl, C₁ -C₂ haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂-C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl,amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl,methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁ -C₂ alkyl)-aminocarbonyl or[di(C₁ -C₂ alkyl)amino]carbonyl, or R⁸ is phenyl, benzyl, phenoxy,benzyloxy or pyridyloxy, each of which is optionally substituted withhalogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃haloalkoxy; and r is an integer of 0 to 7);

dihalopropene compounds wherein A is 2-pyridyl, 3-pyridyl, 4-pyridyl,2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(1,3-thiazolyl),N-(1,2-dihydro-2-oxo)pyridino, 1,3-dioxolanyl, 1,4-benzodioxanyl,2-pyrazyl, 2-benzothiazolyl, 2-benzoxazolyl, 2-benzimidazolyl,2-quinoxalynyl, N-benzimidazolyl, 2-quinolyl, 3-quinolyl orN-phthalimido, each of which is optionally substituted with (R⁸)_(r)(wherein R⁸ and r are each as defined above);

dihalopropene compounds wherein R² and R³ are independently halogen orC₁ -C₃ alkyl, and t is 0;

dihalopropene compounds wherein R² and R³ are independently chlorine,bromine, methyl, ethyl or isopropyl, and t is 0;

dihalopropene compounds wherein R² and R³ are both chlorine, and t is 0;

dihalopropene compounds wherein R² is chlorine, R³ is methyl, and t is0;

dihalopropene compounds wherein R² is ethyl, R³ is methyl, and t is 0;

dihalopropene compounds wherein R² and R³ are both bromine, and t is 0;

dihalopropene compounds wherein R² and R³ are both ethyl, and t is 0;

dihalopropene compounds wherein R² and R³ are independently halogen orC₁ -C₃ alkyl, t is 1 or 2, and R¹⁰ is halogen or C₁ -C₃ alkyl;

dihalopropene compounds wherein R² and R³ are independently halogen orC₁ -C₃ alkyl, t is 1 or 2, and R¹⁰ is halogen;

dihalopropene compounds wherein Y and Z are both oxygen;

dihalopropene compounds wherein R¹ is Q₁, p is 1 to 6, and A is2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl,3-furanyl, 5-(1,3-thiazolyl), N-(1,2dihydro-2-oxo)pyridino,1,3-dioxolanyl or N-phthalimido, each of which is optionally substitutedwith (R⁸)_(r) (wherein R⁸ and r are each as defined above);

dihalopropene compounds wherein R¹ is Q₁, p is 1 to 6, R⁵, R⁶ and R⁷ areall hydrogen, and A is 1,3-dioxolanyl optionally substituted with(R⁸)_(r) (wherein R⁸ and r are each as defined above);

dihalopropene compounds wherein R¹ is Q₁, p is 1 to 4, R⁵, R⁶ and R⁷ areall hydrogen, and A is 1,3-dioxolanyl optionally substituted with(R⁸)_(r) (wherein R⁸ and r are each as defined above);

dihalopropene compounds wherein R¹ is Q₁, p is 0, and A is 2-pyridyl,4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl,5-(1,3-thiazolyl), 1,3-dioxolanyl or 1,4-benzodioxolanyl, each of whichis optionally substituted with (R )r (wherein R⁸ and r are each asdefined above);

dihalopropene compounds wherein R¹ is Q₂ ;

dihalopropene compounds wherein R¹ is Q₂, and A is 2-pyridyl, 3-pyridyl,4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl,5-(1,3-thiazolyl), 2-pyradyl, 2-benzothiazolyl, 2-benzoxazolyl,2-benzimidazolyl, 2-quinoxalynyl, N-benzimidazolyl, 2-quinolynyl or3-quinolyl, each of which is optionally substituted with (R⁸)_(r)(wherein R⁸ and r are each as defined above);

dihalopropene compounds wherein R¹ is Q₂, p is 1 to 4, and A is2-pyridyl optionally substituted with (R⁸)_(r) (wherein R⁸ and r areeach as defined above);

dihalopropene compounds wherein R¹ is Q₂, p is 1 to 4, R⁵, R⁶ and R⁷ areall hydrogen, and A is 2-pyridyl optionally substituted with (R⁸)_(r)(wherein R⁸ and r are each as defined above);

dihalopropene compounds wherein R¹ is Q₂, p is 1 to 4, R⁵, R⁶ and R⁷ areall hydrogen, A is 2-pyridyl optionally substituted with (R⁸)_(r)(wherein R⁸ is halogen or C₁ -C₃ haloalkyl and r is as defined above);

dihalopropene compounds wherein R¹ is Q₂, p is 2 or 3, R⁵, R⁶ and R⁷ areall hydrogen, A is 2-pyridyl optionally substituted with (R⁸)_(r)(wherein R⁸ is halogen or C₁ -C₃ haloalkyl and r is as defined above);

dihalopropene compounds wherein R¹ is Q₂, p is 2 or 3, R⁵, R⁶ and R⁷ areall hydrogen, A is 2-pyridyl optionally substituted with (R⁸)_(r)(wherein R⁸ is halogen or trifluoromethyl and r is as defined above);and

dihalopropene compounds wherein R¹ is Q₂, p is 2 or 3, R⁵, R⁶ and R⁷ areall hydrogen, B is oxygen, A is 2-pyridyl optionally substituted with(R⁸)_(r) (wherein R⁸ is halogen or trifluoromethyl and r is as definedabove).

The following are particularly preferred examples of the presentcompound wherein numbers in parentheses are the corresponding compoundnumbers used below.

(36)3,5-Dichloro-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene;

(47)3-Ethyl-5-methyl-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene;and

(49) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-pyridylamino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.

The present compounds can be produced, for example, by the followingproduction processes A-H.

(Production Process A)

In this process, a compound of the general formula: ##STR4## wherein R¹,R², R³, R¹⁰, t, Y and Z are each as defined above, is reacted with ahalide compound of the general formula:

    L--CH.sub.2 CH═CX.sub.2                                [IV]

wherein X is as defined above and L is halogen (e.g., chlorine, bromine,iodine), mesyloxy or tosyloxy.

The reaction is preferably effected in an inert solvent in the presenceof a suitable base.

Examples of the solvent that can be used are ketones such as acetone,methyl ethyl ketone and cyclohexanone; ethers such as1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄)ether (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide,dimethylsulfoxide, hexamethylphosphoric triamide, sulforane,acetonitrile, nitromethane; halogenated hydrocarbons such asdichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene;hydrocarbons such as toluene, benzene and xylene; and water. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metalsor alkaline earth metals, such as lithium hydroxide, sodium hydroxide,potassium hydroxide and calcium hydroxide; carbonates of alkali metalsor alkaline earth metals, such as lithium carbonate, potassiumcarbonate, sodium carbonate and calcium carbonate; hydrides of alkalimetals or alkaline earth metals, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride; alkali metal alkoxides(e.g., C₁ -C₄), such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide; and organic bases such as triethylamine and pyridine. Ifnecessary, catalysts such as ammonium salts (e.g.,triethylbenzylammonium chloride) may be added to the reaction system ata ratio of 0.01 to 1 mole per mole of the compound of the generalformula [III].

The reaction temperature is usually set within the range of -20° C. to150° C. or the boiling point of a solvent used in the reaction,preferably -5° C. to 100° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials and bases to be used in thereaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out, if necessary, by anordinary technique such as chromatography, distillation orrecrystallization.

(Production Process B for the present compounds wherein Y is oxygen)

In this process, a compound of the general formula [III] is reacted withan alcohol compound of the general formula:

    HO--CH.sub.2 CH═CX.sub.2                               [V]

wherein X is as defined above.

The reaction is preferably effected in an inert solvent, if necessary,in the presence of a suitable dehydrating agent.

Examples of the dehydrating agent which can be used aredicyclohexylcarbodiimide, and dialkyl (e.g., C₁ -C₄) azodicarboxylates(e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl(e.g., C₁ -C₂₀) phosphine or triarylphosphine (e.g., triphenylphosphine,trioctylphosphine, tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such ascarbon tetrachloride, dichloromethane, chlorobenzene anddichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the starting materials and dehydrating agents to beused in the reaction can be freely determined, but it is favorable toeffect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

(Production Process C for the present compounds wherein Y is oxygen)

In this process, an aldehyde compound of the general formula: ##STR5##wherein R¹, R², R³, R¹⁰, t and Z are each as defined above, is reactedwith carbon tetrachloride or carbon tetrabromide.

The reaction is preferably effected in an inert solvent in the presenceof a suitable trialkylphosphine or triarylphosphine, and if necessary,in the presence of metal zinc.

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons(exclusive of carbon tetrabromide and carbon tetrachloride) such asdichloromethane, 1,2-dichloroethane and chlorobenzene.

The reaction temperature is usually set within the range of -30° C. to150° C. or the boiling point of a solvent used in the reaction.

Examples of the trialkyl (e.g., C₁ -C₂₀) phosphine or triarylphosphineare triphenylphosphine and trioctylphosphine. The metal zinc which isused, if necessary, is preferably in dust form.

The molar ratio of the starting materials and reagents to be used in thereaction can be freely determined, but the ratio is preferably such thatcarbon tetrabromide or tetrachloride, trialkylphosphine ortriarylphosphine, and zinc are 2 moles, 2 or 4 moles (2 moles when zincis used), and 2 moles, respectively, per mole of the aldehyde compoundof the general formula [VI], or it is favorable to effect the reactionat a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

(Production Process D for the present compounds wherein Y and Z are bothoxygen)

In this process, a compound of the general formula: ##STR6## wherein R²,R³, R¹⁰, t and X are each as defined above, is reacted with a compoundof the general formula:

    R.sup.1 --L                                                [VIII]

wherein R¹ and L are each as defined above.

The reaction is preferably effected in an inert solvent in the presenceof a suitable base.

Examples of the solvent which can be used are ketones such as acetone,methyl ethyl ketone and cyclohexanone; ethers such as1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄)ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide,dimethylsulfoxide, hexamethylphosphoric triamide, sulforane,acetonitrile, nitromethane; halogenated hydrocarbons such asdichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene;hydrocarbons such as toluene, benzene and xylene; and water. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metalsor alkaline earth metals, such as lithium hydroxide, sodium hydroxide,potassium hydroxide and calcium hydroxide; carbonates of alkali metalsor alkaline earth metals, such as lithium carbonate, potassiumcarbonate, sodium carbonate and calcium carbonate; hydrides of alkalimetals or alkaline earth metals, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride; alkali metal alkoxides(e.g., C₁ -C₄) such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide; organic bases such as triethylarine and pyridine. Ifnecessary, catalysts such as ammonium salts (e.g.,triethylbenzylammonium chloride) may be added to the reaction system ata ratio of 0.01 to 1 mole per mole of the compound of the generalformula [VII].

The reaction temperature is usually set within the range of -20° C. to150° C. or the boiling point of a solvent used in the reaction,preferably -5° C. to 100° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials and dehydrating agents to beused in the reaction can be freely determined, but it is favorable toeffect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

(Production Process E for the present compounds wherein Y and Z are bothoxygen)

In this process, a compound of the general formula [VII] is reacted withan alcohol compound of the general formula:

    R.sup.1 --OH                                               [IX]

wherein R¹ is as defined above.

The reaction is preferably effected in an inert solvent, if necessary,in the presence of a suitable dehydrating agent.

Examples of the dehydrating agent which can be used aredicyclohexylcarboduimide, and dialkyl (es., C₁ -C₄) azodicarboxylates(e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl(e.g., C₁ -C₂₀) phosphine or triarylphosphine (e.g., triphenylphosphine,trioctylphosphine, tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such ascarbon tetrachloride, dichloromethane, chlorobenzene anddichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used inthe reaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

(Production Process F for the present compounds wherein Y and Z are bothoxygen, R¹ is Q₂ or Q₃, and B is B¹ (wherein B¹ is oxygen, sulfur or NR⁹[wherein R⁹ is as defined above]))

In this process, a compound of the general formula: ##STR7## wherein B¹,R², R³, R⁵, R⁶, R⁷, R¹⁰, p, t and X are each as defined above, isreacted with a compound of the geneial formula: ##STR8## wherein A, R¹¹,R¹², L and X are each as defined above.

The reaction is preferably effected in an inert solvent in the presenceof a suitable base.

Examples of the solvent which can be used are ketones such as acetone,methyl ethyl ketone and cyclohexanone; ethers such as1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄)ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide,dimethylsulfoxide, hexamethyiphosphoric triamide, 5 ulforane,acetonitrile, nitromethane; halogenated hydrocarbons such asdichioromethane, chloroform, 1,2-dichloroethane and chlorobenzene;hydrocarbons such as toluene, benzene and xylene; and water. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metalsor alkaline earth metals, such as lithium hydroxide, sodium hydroxide,potassium hydroxide and calcium hydroxide; carbonates of alkali metalsor alkaline earth metals, such as lithium carbonate, potassiumcarbonate, sodium carbonate and calcium carbonate; hydrides of alkalimetals or alkaline earth metals, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride; alkali metal alkoxides(e.g., C₁ -C₄) such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide; organic bases such as triethylamine and pyridine. Ifnecessary, catalysts such as ammonium salts (e.g.,triethylbenzylammonium chloride) may be added to the reaction system ata ratio of 0.01 to 1 mole per mole of the compound of the generalformula [X].

The reaction temperature is usually set within the range of -20° C. to150° C. or the boiling point of a solvent used in the reaction,preferably -5° C. to 100° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials and dehydrating agents to beused in the reaction can be freely determined, but it is favorable toeffect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

(Production Process G for the present compounds wherein Y, Z and B areall oxygen and R¹ is Q₂, Q₃, Q₆ or Q₇)

In this process, an alcohol compound of the general formula: ##STR9##wherein R², R³, R¹⁰, R⁵, R⁶, R⁷, p, t and X are each as defined above,is reacted with compound Q₂₁, Q₃₁, Q₆₁ or Q₇₁ of the general formula:##STR10## wherein R¹¹, R¹², R¹³, R¹⁴, A and s are each as defined above.

The reaction is preferably effected in an inert solvent, if necessary,in the presence of a suitable dehydrating agent.

Examples of the dehydrating agent which can be used aredicyclohexylcarboduimide, and dialkyl (e.g., C₁ -C₄) azodicarboxylates(e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl(e.g., C₁ -C₂₀) phosphine or triarylphosphine (e.g., triphenylphosphine,trioctylphosphine, tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such asbenzene, xylene and toluene; ethers such as diethyl ether, diisopropylether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such ascarbon tetrachloride, dichloromethane, chlorobenzene anddichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used inthe reaction can be freely determined, but it is favorable to effect thereaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

(Production Process H for the present compounds wherein Y and Z are bothoxygen and R¹ is Q₂, Q₃, Q₆ or Q₇)

In this process, a compound of the general formula: ##STR11## whereinR², R³, R⁵, R⁶, R⁷, R¹⁰, X, L, p and t are each as defined above, isreacted with compound Q₂₂, Q₃₂, Q₆₂ or Q₇₂ of the general formula:##STR12## wherein R¹¹, R¹², R¹³, R¹⁴, A, B and s are each as definedabove.

The reaction is preferably effected in an inert solvent in the presenceof a suitable base.

Examples of the solvent which can be used are ketones such as acetone,methyl ethyl ketone and cyclohexanone; ethers such as1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄)ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide,dimethylsulfoxide, hexamethylphosphoric triamide, sulforane,acetonitrile, nitromethane; halogenated hydrocarbons such asdichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene;hydrocarbons such as toluene, benzene and xylene; and water. Ifnecessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metalsor alkaline earth metals, such as lithium hydroxide, sodium hydroxide,potassium hydroxide and calcium hydroxide; carbonates of alkali metalsor alkaline earth metals, such as lithium carbonate, potassiumcarbonate, sodium carbonate and calcium carbonate; hydrides of alkalimetals or alkaline earth metals, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride; alkali metal alkoxides(e.g., C₁ -C₄) such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide; organic bases such as triethylamine and pyridine. Ifnecessary, catalysts such as ammonium salts (e.g.,triethylbenzylammonium chloride) may be added to the reaction system ata ratio of 0.01 to 1 mole per mole of the compound of the generalformula [XIV].

The reaction temperature is usually set within the range of -20° C. to150° C. or the boiling point of a solvent used in the reaction,preferably -5° C. to 100° C. or the boiling point of a solvent used inthe reaction.

The molar ratio of the starting materials and dehydrating agents to beused in the reaction can be freely determined, but it is favorable toeffect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected toordinary post-treatments such as organic solvent extraction andconcentration, and the desired compound of the present invention can beisolated. Further, purification can be carried out by an ordinarytechnique such as chromatography, distillation or recrystallization.

When the present compound has an asymmetry carbon atom, it is to beconstrued to include its optically active isomers ((+)-form and(-)-form) having biological activity and their mixtures at any ratio.When the present compound exhibits geometrical isomerism, it is to beconstrued to include its geometrical isomers (cis-form and transform)and their mixtures at any ratio.

The following are typical examples of the present compound (wherein R¹is as shown in Tables 1 to 46), which are not to be construed to limitthe scope of the present invention. ##STR13##

                  TABLE 1                                                         ______________________________________                                        Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5 R.sup.6                                                                              R.sup.7                                                                            p      (R.sup.8).sub.r                         ______________________________________                                        2          H       H      H    0      H                                       2          H       H      H    1      H                                       2          H       H      H    2      H                                       2          H       H      H    3      H                                       2          H       H      H    4      H                                       2          H       H      H    5      H                                       2          H       H      H    6      H                                       2          H       H      H    0      5-CH.sub.3                              2          H       H      H    1      5-CH.sub.3                              2          H       H      H    2      5-CH.sub.3                              2          H       H      H    3      5-CH.sub.3                              2          H       H      H    4      5-CH.sub.3                              2          H       H      H    5      5-CH.sub.3                              2          H       H      H    6      5-CH.sub.3                              2          H       H      H    0      5-CH.sub.2 OCH.sub.3                    2          H       H      H    1      5-CH.sub.2 OCH.sub.3                    2          H       H      H    2      5-CH.sub.2 OCH.sub.3                    2          H       H      H    3      5-CH.sub.2 OCH.sub.3                    2          H       H      H    4      5-CH.sub.2 OCH.sub.3                    2          H       H      H    0      5-CH.sub.2 CH.sub.3                     2          H       H      H    1      5-CH.sub.2 CH.sub.3                     2          H       H      H    2      5-CH.sub.2 CH.sub.3                     2          H       H      H    3      5-CH.sub.2 CH.sub.3                     2          H       H      H    4      5-CH.sub.2 CH.sub.3                     2          H       H      H    5      5-CH.sub.2 CH.sub.3                     2          H       H      H    6      5-CH.sub.2 CH.sub.3                     2          H       H      CH.sub.3                                                                           0      H                                       2          H       H      CH.sub.3                                                                           0      5-CH.sub.3                              2          H       H      H    0      5-CHO                                   2          H       H      H    1      5-CHO                                   2          H       H      H    2      5-CHO                                   2          H       H      H    3      5-CHO                                   2          H       H      H    4      5-CHO                                   2          H       H      H    5      5-CHO                                   2          H       H      H    6      5-CHO                                   2          H       H      H    0      5-NO.sub.2                              2          H       H      H    1      5-NO.sub.2                              2          H       H      H    2      5-NO.sub.2                              2          H       H      H    3      5-NO.sub.2                              2          H       H      H    4      5-NO.sub.2                              2          H       H      H    5      5-NO.sub.2                              2          H       H      H    6      5-NO.sub.2                              2          H       H      H    0      3-CO.sub.2 CH.sub.3                     3          H       H      H    0      H                                       3          H       H      H    1      H                                       3          H       H      H    2      H                                       3          H       H      H    3      H                                       3          H       H      H    4      H                                       3          H       H      H    5      H                                       3          H       H      H    6      H                                       3          H       H      H    0      2-CH.sub.3                              3          H       H      H    1      2-CH.sub.3                              3          H       H      H    2      2-CH.sub.3                              3          H       H      H    3      2-CH.sub.3                              3          H       H      H    4      2-CH.sub.3                              3          H       H      H    5      2-CH.sub.3                              3          H       H      H    6      2-CH.sub.3                              3          H       H      H    0      2,5-(CH.sub.3).sub.2                    3          H       H      H    1      2,5-(CH.sub.3).sub.2                    3          H       H      H    2      2,5-(CH.sub.3).sub.2                    3          H       H      H    3      2,5-(CH.sub.3).sub.2                    3          H       H      H    4      2,5-(CH.sub.3).sub.2                    3          H       H      H    5      2,5-(CH.sub.3).sub.2                    3          H       H      H    6      2,5-(CH.sub.3).sub.2                    3          H       H      H    0      2,4-(CH.sub.3).sub.2                    3          H       H      H    1      2,4-(CH.sub.3).sub.2                    3          H       H      H    2      2,4-(CH.sub.3).sub.2                    3          H       H      H    3      2,4-(CH.sub.3).sub.2                    3          H       H      H    4      2,4-(CH.sub.3).sub.2                    3          H       H      H    5      2,4-(CH.sub.3).sub.2                    3          H       H      H    6      2,4-(CH.sub.3).sub.2                    ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR14##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5                                                                              R.sup.6                                                                              R.sup.7                                                                           p     (R.sup.8).sub.r                                                                      B                                   ______________________________________                                        2          H      H      H   1     H      COO                                 2          H      H      H   2     H      COO                                 2          H      H      H   3     H      COO                                 2          H      H      H   1     5-CH.sub.3                                                                           COO                                 2          H      H      H   1     5-C.sub.2 H.sub.5                                                                    COO                                 2          H      H      H   1     5-Br   COO                                 2          H      H      H   2     5-CH.sub.3                                                                           COO                                 2          H      H      H   2     5-C.sub.2 H.sub.5                                                                    COO                                 2          H      H      H   2     5-Br   COO                                 2          H      H      H   3     5-CH.sub.3                                                                           COO                                 2          H      H      H   3     5-C.sub.2 H.sub.5                                                                    COO                                 2          H      H      H   3     5-CH.sub.3                                                                           COO                                 3          H      H      H   1     H      COO                                 3          H      H      H   2     H      COO                                 3          H      H      H   3     H      COO                                 ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR15##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring     R.sup.5 R.sup.6                                                                              R.sup.7                                                                              p     (R.sup.8).sub.r                          ______________________________________                                        2        H       H      H      0     H                                        2        H       H      H      1     H                                        2        H       H      H      2     H                                        2        H       H      H      3     H                                        2        H       H      H      4     H                                        2        H       H      H      5     H                                        2        H       H      H      6     H                                        2        H       H      H      0     5-CH.sub.3                               2        H       H      H      1     5-CH.sub.3                               2        H       H      H      2     5-CH.sub.3                               2        H       H      H      3     5-CH.sub.3                               2        H       H      H      4     5-CH.sub.3                               2        H       H      H      5     5-CH.sub.3                               2        H       H      H      6     5-CH.sub.3                               2        H       H      H      0     5-Cl                                     2        H       H      H      1     5-Cl                                     2        H       H      H      2     5-Cl                                     2        H       H      H      3     5-Cl                                     2        H       H      H      4     5-Cl                                     2        H       H      H      5     5-Cl                                     2        H       H      H      6     5-Cl                                     2        H       H      H      0     5-Br                                     2        H       H      H      1     5-Br                                     2        H       H      H      2     5-Br                                     2        H       H      H      3     5-Br                                     2        H       H      H      4     5-Br                                     2        H       H      H      5     5-Br                                     2        H       H      H      6     5-Br                                     2        H       H      H      0     5-NO.sub.2                               2        H       H      H      1     5-NO.sub.2                               2        H       H      H      2     5-NO.sub.2                               2        H       H      H      3     5-NO.sub.2                               2        H       H      H      4     5-NO.sub.2                               2        H       H      H      5     5-NO.sub.2                               2        H       H      H      6     5-NO.sub.2                               2        H       H      H      0     5-NH.sub.2                               2        H       H      H      1     5-NH.sub.2                               2        H       H      H      2     5-NH.sub.2                               2        H       H      H      3     5-NH.sub.2                               2        H       H      H      4     5-NH.sub.2                               2        H       H      H      5     5-NH.sub.2                               2        H       H      H      6     5-NH.sub.2                               2        H       H      H      0     5-NHCOCH.sub.3                           2        H       H      H      1     5-NHCOCH.sub.3                           2        H       H      H      2     5-NHCOCH.sub.3                           2        H       H      H      3     5-NHCOCH.sub.3                           2        H       H      H      4     5-NHCOCH.sub.3                           2        H       H      H      5     5-NHCOCH.sub.3                           2        H       H      H      6     5-NHCOCH.sub.3                           2        H       H      H      0     5-NHCOCF.sub.3                           2        H       H      H      1     5-NHCOCF.sub.3                           2        H       H      H      2     5-NHCOCF.sub.3                           2        H       H      H      3     5-NHCOCF.sub.3                           2        H       H      H      4     5-NHCOCF.sub.3                           2        H       H      H      5     5-NHCOCF.sub.3                           2        H       H      H      6     5-NHCOCF.sub.3                           2        H       H      CH.sub.3                                                                             0     3-CH.sub.3                               2        H       H      CH.sub.3                                                                             0     5-Cl                                     2        H       H      CH.sub.3                                                                             0     5-Br                                     2        H       H      CH.sub.2 CH.sub.3                                                                    0     H                                        2        H       H      H      0     3-CH.sub.3                               2        H       H      H      1     3-CH.sub.3                               2        H       H      H      0     5-NH.sub.2                               2        H       H      H      2     3-CH.sub.3                               2        H       H      H      3     3-CH.sub.3                               2        H       H      H      4     3-CH.sub.3                               2        H       H      H      5     3-CH.sub.3                               2        H       H      H      6     3-CH.sub.3                               2        H       H      H      0     4-Br                                     2        H       H      H      1     4-Br                                     2        H       H      H      2     4-Br                                     2        H       H      H      3     4-Br                                     2        H       H      H      4     4-Br                                     2        H       H      H      5     4-Br                                     2        H       H      H      6     4-Br                                     3        H       H      H      0     H                                        3        H       H      H      1     H                                        3        H       H      H      2     H                                        3        H       H      H      3     H                                        3        H       H      H      4     H                                        3        H       H      H      5     H                                        3        H       H      H      6     H                                        3        H       H      CH.sub.3                                                                             0     H                                        3        H       H      CH.sub.3                                                                             0     2,5-(CH.sub.3).sub.2                     ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR16##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring     B       R.sup.5                                                                              R.sup.6                                                                            R.sup.7                                                                           p     (R.sup.8).sub.r                                                                      F                               ______________________________________                                        3        S       H      H    H   0     2-CH.sub.3                                                                           O                               2        SO.sub.2                                                                              H      H    H   0     H      S                               2        SO.sub.2                                                                              H      H    H   1     H      S                               2        SO.sub.2                                                                              H      H    H   2     H      S                               2        SO.sub.2                                                                              H      H    H   3     H      S                               2        SO.sub.2                                                                              H      H    H   4     H      S                               2        SO.sub.2                                                                              H      H    H   5     H      S                               2        SO.sub.2                                                                              H      H    H   6     H      S                               2        COO     H      H    H   2     H      S                               2        COO     H      H    H   3     H      S                               2        COO     H      H    H   4     H      S                               3        COO     H      H    H   2     H      S                               3        COO     H      H    H   3     H      S                               3        COO     H      H    H   4     H      S                               2        COO     H      H    H   2     5-CH.sub.3                                                                           S                               2        COO     H      H    H   3     5-CH.sub.3                                                                           S                               2        COO     H      H    H   4     5-CH.sub.3                                                                           S                               ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR17##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        2           H       H       H   0       H                                     2           H       H       H   1       H                                     2           H       H       H   2       H                                     2           H       H       H   3       H                                     2           H       H       H   4       H                                     2           H       H       H   5       H                                     2           H       H       H   6       H                                     ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR18##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        2           H       H       H   0       H                                     2           H       H       H   1       H                                     2           H       H       H   2       H                                     2           H       H       H   3       H                                     2           H       H       H   4       H                                     2           H       H       H   5       H                                     2           H       H       H   6       H                                     ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR19##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5 R.sup.6                                                                              R.sup.7                                                                           p      (R.sup.8).sub.r                          ______________________________________                                        3          H       H      H   0      H                                        3          H       H      H   1      H                                        3          H       H      H   2      H                                        3          H       H      H   3      H                                        3          H       H      H   4      H                                        3          H       H      H   5      H                                        3          H       H      H   6      H                                        3          H       H      H   0      5-Cl                                     3          H       H      H   1      5-Cl                                     3          H       H      H   2      5-Cl                                     3          H       H      H   3      5-Cl                                     3          H       H      H   4      5-Cl                                     3          H       H      H   5      5-Cl                                     3          H       H      H   6      5-Cl                                     3          H       H      H   0      5-Br                                     3          H       H      H   1      5-Br                                     3          H       H      H   2      5-Br                                     3          H       H      H   3      5-Br                                     3          H       H      H   4      5-Br                                     3          H       H      H   5      5-Br                                     3          H       H      H   6      5-Br                                     5          H       H      H   0      H                                        5          H       H      H   1      H                                        5          H       H      H   2      H                                        5          H       H      H   3      H                                        5          H       H      H   4      H                                        5          H       H      H   5      H                                        5          H       H      H   6      H                                        5          H       H      H   0      3-Cl                                     5          H       H      H   1      3-Cl                                     5          H       H      H   2      3-Cl                                     5          H       H      H   3      3-Cl                                     5          H       H      H   4      3-Cl                                     5          H       H      H   5      3-Cl                                     5          H       H      H   6      3-Cl                                     5          H       H      H   0      3-Br                                     5          H       H      H   1      3-Br                                     5          H       H      H   2      3-Br                                     5          H       H      H   3      3-Br                                     5          H       H      H   4      3-Br                                     5          H       H      H   5      3-Br                                     5          H       H      H   6      3-Br                                     4          H       H      H   0      H                                        4          H       H      H   1      H                                        4          H       H      H   2      H                                        4          H       H      H   3      H                                        4          H       H      H   4      H                                        4          H       H      H   5      H                                        4          H       H      H   6      H                                        4          H       H      H   0      3,5-(CH.sub.3).sub.2                     ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR20##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        3           H       H       H   0       H                                     3           H       H       H   1       H                                     3           H       H       H   2       H                                     3           H       H       H   3       H                                     3           H       H       H   4       H                                     3           H       H       H   5       H                                     3           H       H       H   6       H                                     3           H       H       H   0       5-Cl                                  3           H       H       H   1       5-Cl                                  3           H       H       H   2       5-Cl                                  3           H       H       H   3       5-Cl                                  3           H       H       H   4       5-Cl                                  3           H       H       H   5       5-Cl                                  3           H       H       H   6       5-Cl                                  3           H       H       H   0       5-Br                                  3           H       H       H   1       5-Br                                  3           H       H       H   2       5-Br                                  3           H       H       H   3       5-Br                                  3           H       H       H   4       5-Br                                  3           H       H       H   5       5-Br                                  3           H       H       H   6       5-Br                                  ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR21##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5 R.sup.6 R.sup.7                                                                            p      (R.sup.8).sub.r                        ______________________________________                                        4          H       H       H    0      H                                      4          H       H       H    1      H                                      4          H       H       H    2      H                                      4          H       H       H    3      H                                      4          H       H       H    4      H                                      4          H       H       H    5      H                                      4          H       H       H    6      H                                      4          H       H       H    0      2-Cl                                   4          H       H       H    1      2-Cl                                   4          H       H       H    2      2-Cl                                   4          H       H       H    3      2-Cl                                   4          H       H       H    4      2-Cl                                   4          H       H       H    5      2-Cl                                   4          H       H       H    6      2-Cl                                   4          H       H       H    0      2-Br                                   4          H       H       H    1      2-Br                                   4          H       H       H    2      2-Br                                   4          H       H       H    3      2-Br                                   4          H       H       H    4      2-Br                                   4          H       H       H    5      2-Br                                   4          H       H       H    6      2-Br                                   5          H       H       H    0      H                                      5          H       H       H    1      H                                      5          H       H       H    2      H                                      5          H       H       H    3      H                                      5          H       H       H    4      H                                      5          H       H       H    5      H                                      5          H       H       H    6      H                                      5          H       H       H    0      2-Cl                                   5          H       H       H    1      2-Cl                                   5          H       H       H    2      2-Cl                                   5          H       H       H    3      2-Cl                                   5          H       H       H    4      2-Cl                                   5          H       H       H    5      2-Cl                                   5          H       H       H    6      2-Cl                                   5          H       H       H    0      2-Br                                   5          H       H       H    1      2-Br                                   5          H       H       R    2      2-Br                                   5          H       H       H    3      2-Br                                   5          H       H       H    4      2-Br                                   5          H       H       H    5      2-Br                                   5          H       H       H    6      2-Br                                   5          H       H       H    1      4-CH.sub.3                             5          H       H       CH.sub.3                                                                           0      4-CH.sub.3                             2          H       H       CH.sub.3                                                                           0      H                                      ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR22##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring     R.sup.5 R.sup.6                                                                              R.sup.7                                                                            p     (R.sup.8).sub.r                            ______________________________________                                        1        H       H      H    0     H                                          1        H       H      H    1     H                                          1        H       H      H    2     H                                          1        H       H      H    3     H                                          1        H       H      H    4     H                                          1        H       H      H    5     H                                          1        H       H      H    6     H                                          1        H       H      H    0     2-CH.sub.2 CH.sub.3                        1        H       H      H    1     2-CH.sub.2 CH.sub.3                        1        H       H      H    2     2-CH.sub.2 CH.sub.3                        1        H       H      H    3     2-CH.sub.2 CH.sub.3                        1        H       H      H    4     2-CH.sub.2 CH.sub.3                        1        H       H      H    5     2-CH.sub.2 CH.sub.3                        1        H       H      H    6     2-CH.sub.2 CH.sub.3                        1        H       H      H    0     2,5-(CH.sub.3).sub.2                       1        H       H      H    1     2,5-(CH.sub.3).sub.2                       1        H       H      H    2     2,5-(CH.sub.3).sub.2                       1        H       H      H    3     2,5-(CH.sub.3).sub.2                       1        H       H      H    4     2,5-(CH.sub.3).sub.2                       1        H       H      H    5     2,5-(CH.sub.3).sub.2                       1        H       H      H    6     2,5-(CH.sub.3).sub.2                       1        H       H      H    0     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    1     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    2     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    3     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    4     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    5     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    6     2,4-(CH.sub.3).sub.2, 3-CH.sub.2                                              CH.sub.3                                   1        H       H      H    0     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    1     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    2     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    3     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    4     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    5     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    6     2,4-(CH.sub.3).sub.2, 3-COCH.sub.3         1        H       H      H    0     2-COCH.sub.3                               1        H       H      H    1     2-COCH.sub.3                               1        H       H      H    2     2-COCH.sub.3                               1        H       H      H    3     2-COCH.sub.3                               1        H       H      H    4     2-COCH.sub.3                               1        H       H      H    5     2-COCH.sub.3                               1        H       H      H    6     2-COCH.sub.3                               1        H       H      H    0     2-CHO                                      1        H       H      H    1     2-CHO                                      1        H       H      H    2     2-CHO                                      1        H       H      H    3     2-CHO                                      1        H       H      H    4     2-CHO                                      1        H       H      H    5     2-CHO                                      1        H       H      H    6     2-CHO                                      2        H       H      CH.sub.3                                                                           0     2,4-(CH.sub.3).sub.2                       2        H       H      CH.sub.3                                                                           0     H                                          2        H       H      CH.sub.3                                                                           0     1-CH.sub.3                                 3        H       H      CH.sub.3                                                                           0     1-CH.sub.3                                 3        H       H      H    0     H                                          3        H       H      H    1     H                                          3        H       H      H    2     H                                          3        H       H      H    3     H                                          3        H       H      H    4     H                                          3        H       H      H    5     H                                          3        H       H      H    6     H                                          2        H       H      H    0     H                                          2        H       H      H    1     1-CH.sub.3                                 2        H       H      H    2     1-CH.sub.3                                 2        H       H      H    3     1-CH.sub.3                                 2        H       H      H    4     1-CH.sub.3                                 2        H       H      H    5     1-CH.sub.3                                 2        H       H      H    6     1-CH.sub.3                                 2        H       H      H    0     3,5-(CH.sub.3).sub.2                       2        H       H      H    1     3,5-(CH.sub.3).sub.2                       2        H       H      H    2     3,5-(CH.sub.3).sub.2                       2        H       H      H    3     3,5-(CH.sub.3).sub.2                       2        H       H      H    4     3,5-(CH.sub.3).sub.2                       2        H       H      H    5     3,5-(CH.sub.3).sub.2                       2        H       H      H    6     3,5-(CH.sub.3).sub.2                       2        H       H      H    0     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    1     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    2     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    3     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    4     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    5     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    6     3,4,5-(CH.sub.3).sub.3                     2        H       H      H    0     3,4-(C.sub.2 H.sub.5).sub.2,                                                  5-CH.sub.3                                 2        H       H      H    1     3,4-(C.sub.2 H.sub.5).sub.2,                                                  5-CH.sub.3                                 2        H       H      H    2     3,4-(C.sub.2 H.sub.5).sub.2,                                                  5-CH.sub.3                                 2        H       H      H    3     3,4-(C.sub.2 H.sub.5).sub.2,                                                  5-CH.sub.3                                 2        H       H      H    4     3,4-(C.sub.2 H.sub.5).sub.2,                                                  5-CH.sub.3                                 2        H       H      H    5     3,4-(C.sub.2 H.sub.5).sub.2,                                                  5-CH.sub.3                                 2        H       H      H    6     3,4-(C.sub.2 H.sub.5).sub.2,               ______________________________________                                                                           5-CH.sub.3                             

                  TABLE 11                                                        ______________________________________                                         ##STR23##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        2           H       H       H   0       5-Cl                                  2           H       H       H   1       5-Cl                                  2           H       H       H   2       5-Cl                                  2           H       H       H   3       5-Cl                                  2           H       H       H   4       5-Cl                                  2           H       H       H   5       5-Cl                                  2           H       H       H   6       5-Cl                                  2           H       H       H   0       5-Br                                  2           H       H       H   1       5-Br                                  2           H       H       H   2       5-Br                                  2           H       H       H   3       5-Br                                  2           H       H       H   4       5-Br                                  2           H       H       H   5       5-Br                                  2           H       H       H   6       5-Br                                  2           H       H       H   0       5-Cl                                  2           H       H       H   1       5-Cl                                  2           H       H       H   2       5-Cl                                  2           H       H       H   3       5-Cl                                  2           H       H       H   4       5-Cl                                  2           H       H       H   5       5-Cl                                  2           H       H       H   6       5-Cl                                  2           H       H       H   0       5-Br                                  2           H       H       H   1       5-Br                                  2           H       H       H   2       5-Br                                  2           H       H       H   3       5-Br                                  2           H       H       H   4       5-Br                                  2           H       H       H   5       5-Br                                  2           H       H       H   6       5-Br                                  ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR24##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       B       R.sup.5                                                                              R.sup.6                                                                             R.sup.7                                                                           p      (R.sup.8).sub.r                    ______________________________________                                        2          O       H      H     H   0      5-CH.sub.3                         2          O       H      H     H   1      5-CH.sub.3                         2          O       H      H     H   2      5-CH.sub.3                         2          O       H      H     H   3      5-CH.sub.3                         2          O       H      H     H   4      5-CH.sub.3                         2          O       H      H     H   5      5-CH.sub.3                         2          O       H      H     H   6      5-CH.sub.3                         2          O       H      H     H   0      5-CF.sub.3                         2          O       H      H     H   1      5-CF.sub.3                         2          O       H      H     H   2      5-CF.sub.3                         2          O       H      H     H   3      5-CF.sub.3                         2          O       H      H     H   4      5-CF.sub.3                         2          O       H      H     H   5      5-CF.sub.3                         2          O       H      H     H   6      5-CF.sub.3                         2          O       H      H     H   0      5-Cl                               2          O       H      H     H   1      5-Cl                               2          O       H      H     H   2      5-Cl                               2          O       H      H     H   3      5-Cl                               2          O       H      H     H   4      5-Cl                               2          O       H      H     H   5      5-Cl                               2          O       H      H     H   6      5-Cl                               2          O       H      H     H   0      5-Br                               2          O       H      H     H   1      5-Br                               2          O       H      H     H   2      5-Br                               2          O       H      H     H   3      5-Br                               2          O       H      H     H   4      5-Br                               2          O       H      H     H   5      5-Br                               2          O       H      H     H   6      5-Br                               2          S       H      H     H   0      5-CH.sub.3                         2          S       H      H     H   1      5-CH.sub.3                         2          S       H      H     H   2      5-CH.sub.3                         2          S       H      H     H   3      5-CH.sub.3                         2          S       H      H     H   4      5-CH.sub.3                         2          S       H      H     H   5      5-CH.sub.3                         2          S       H      H     H   6      5-CH.sub.3                         2          S       H      H     H   0      5-CF.sub.3                         2          S       H      H     H   1      5-CF.sub.3                         2          S       H      H     H   2      5-CF.sub.3                         2          S       H      H     H   3      5-CF.sub.3                         2          S       H      H     H   4      5-CF.sub.3                         2          S       H      H     H   5      5-CF.sub.3                         2          S       H      H     H   6      5-CF.sub.3                         2          S       H      H     H   0      5-Cl                               2          S       H      H     H   1      5-Cl                               2          S       H      H     H   2      5-Cl                               2          S       H      H     H   3      5-Cl                               2          S       H      H     H   4      5-Cl                               3          S       H      H     H   5      5-Cl                               3          S       H      H     H   6      5-Cl                               3          S       H      H     H   0      5-Br                               3          S       H      H     H   1      5-Br                               3          S       H      H     H   2      5-Br                               3          S       H      H     H   3      5-Br                               3          S       H      H     H   4      5-Br                               2          S       H      H     H   5      5-Br                               2          S       H      H     H   6      5-Br                               ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR25##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5                                                                              R.sup.6                                                                              R.sup.7                                                                           p     (R.sup.8).sub.r                            ______________________________________                                        1          H      H      H   0     H                                          1          H      H      H   1     H                                          1          H      H      H   2     H                                          1          H      H      H   3     H                                          1          H      H      H   4     H                                          1          H      H      H   5     H                                          1          H      H      H   6     H                                          1          H      H      H   0     3-CH.sub.3                                 1          H      H      H   1     3-CH.sub.3                                 1          H      H      H   2     3-CH.sub.3                                 1          H      H      H   3     3-CH.sub.3                                 1          H      H      H   4     3-CH.sub.3                                 1          H      H      H   5     3-CH.sub.3                                 1          H      H      H   6     3-CH.sub.3                                 1          H      H      H   0     4-CH.sub.3                                 1          H      H      H   1     4-CH.sub.3                                 1          H      H      H   2     4-CH.sub.3                                 1          H      H      H   3     4-CH.sub.3                                 1          H      H      H   4     4-CH.sub.3                                 1          H      H      H   5     4-CH.sub.3                                 1          H      H      H   6     4-CH.sub.3                                 1          H      H      H   0     4-Br                                       1          H      H      H   1     4-Br                                       1          H      H      H   2     4-Br                                       1          H      H      H   3     4-Br                                       1          H      H      H   4     4-Br                                       1          H      H      H   5     4-Br                                       1          H      H      H   6     4-Br                                       1          H      H      H   0     4-I                                        1          H      H      H   1     4-I                                        1          H      H      H   2     4-I                                        1          H      H      H   3     4-I                                        1          H      H      H   4     4-I                                        1          H      H      H   5     4-I                                        1          H      H      H   6     4-I                                        1          H      H      H   0     3,5-(CH.sub.3).sub.2                       1          H      H      H   1     3,5-(CH.sub.3).sub.2                       1          H      H      H   2     3,5-(CH.sub.3).sub.2                       1          H      H      H   3     3,5-(CH.sub.3).sub.2                       1          H      H      H   4     3,5-(CH.sub.3).sub.2                       1          H      H      H   5     3,5-(CH.sub.3).sub.2                       1          H      H      H   6     3,5-(CH.sub.3).sub.2                       1          H      H      H   0     3-CH.sub.3, 4-Br                           1          H      H      H   1     3-CH.sub.3, 4-Br                           1          H      H      H   2     3-CH.sub.3, 4-Br                           1          H      H      H   3     3-CH.sub.3, 4-Br                           1          H      H      H   4     3-CH.sub.3, 4-Br                           1          H      H      H   5     3-CH.sub.3, 4-Br                           1          H      H      H   6     3-CH.sub.3, 4-Br                           1          H      H      H   0     3,5-(CH.sub.3).sub.2, 4-Br                 1          H      H      H   1     3,5-(CH.sub.3).sub.2, 4-Br                 1          H      H      H   2     3,5-(CH.sub.3).sub.2, 4-Br                 1          H      H      H   3     3,5-(CH.sub.3).sub.2, 4-Br                 1          H      H      H   4     3,5-(CH.sub.3).sub.2, 4-Br                 1          H      H      H   5     3,5-(CH.sub.3).sub.2, 4-Br                 1          H      H      H   6     3,5-(CH.sub.3).sub.2, 4-Br                 4          H      H      H   0     H                                          ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                         ##STR26##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring    B      R.sup.5                                                                              R.sup.6                                                                            R.sup.7                                                                           p     (R.sup.8).sub.r                          ______________________________________                                        4       NH     H      H    H   0     5-CH.sub.3, 1-CH.sub.3, 2-C.sub.6                                             H.sub.5                                  5       NH     H      H    H   0     1-CH.sub.2 CH.sub.3                      5       NH     H      H    H   1     1-CH.sub.2 CH.sub.3                      5       NH     H      H    H   2     1-CH.sub.2 CH.sub.3                      5       NH     H      H    H   3     1-CH.sub.2 CH.sub.3                      5       NH     H      H    H   4     1-CH.sub.2 CH.sub.3                      5       NH     H      H    H   5     1-CH.sub.2 CH.sub.3                      5       NH     H      H    H   6     1-CH.sub.2 CH.sub.3                      ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                         ##STR27##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5 R.sup.6                                                                              R.sup.7                                                                            p      (R.sup.8).sub.r                         ______________________________________                                        1          H       H      H    0      H                                       1          H       H      H    1      H                                       1          H       H      H    2      H                                       1          H       H      H    3      H                                       1          H       H      H    4      H                                       1          H       H      H    5      H                                       1          H       H      H    6      H                                       1          H       H      H    0      2-CH.sub.3                              1          H       H      H    1      2-CH.sub.3                              1          H       H      H    2      2-CH.sub.3                              1          H       H      H    3      2-CH.sub.3                              1          H       H      H    4      2-CH.sub.3                              1          H       H      H    5      2-CH.sub.3                              1          H       H      H    6      2-CH.sub.3                              1          H       H      H    1      2-CH.sub.2 CH.sub.3                     1          H       H      H    0      2-CH.sub.2 CH.sub.3                     1          H       H      H    2      2-CH.sub.2 CH.sub.3                     1          H       H      H    3      2-CH.sub.2 CH.sub.3                     1          H       H      H    4      2-CH.sub.2 CH.sub.3                     1          H       H      H    5      2-CH.sub.2 CH.sub.3                     1          H       H      H    6      2-CH.sub.2 CH.sub.3                     1          H       H      H    0      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    1      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    2      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    3      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    4      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    5      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    6      2-CH.sub.2 CH.sub.2 CH.sub.3            1          H       H      H    0      2-CH(CH.sub.3).sub.2                    1          H       H      H    1      2-CH(CH.sub.3).sub.2                    1          H       H      H    2      2-CH(CH.sub.3).sub.2                    1          H       H      H    3      2-CH(CH.sub.3).sub.2                    1          H       H      H    4      2-CH(CH.sub.3).sub.2                    1          H       H      H    5      2-CH(CH.sub.3).sub.2                    1          H       H      H    6      2-CH(CH.sub.3).sub.2                    1          H       H      H    0      2-CH(CH.sub.3).sub.2                    1          H       H      H    1      4,5-Cl.sub.2                            1          H       H      H    2      4,5-Cl.sub.2                            1          H       H      H    3      4,5-Cl.sub.2                            1          H       H      H    4      4,5-Cl.sub.2                            1          H       H      H    5      4,5-Cl.sub.2                            1          H       H      H    6      4,5-Cl.sub.2                            1          H       H      H    0      2,4,5-Cl.sub.3                          1          H       H      H    1      2,4,5-Cl.sub.3                          1          H       H      H    2      2,4,5-Cl.sub.3                          1          H       H      H    3      2,4,5-Cl.sub.3                          1          H       H      H    4      2,4,5-Cl.sub.3                          1          H       H      H    5      2,4,5-Cl.sub.3                          1          H       H      H    6      2,4,5-Cl.sub.3                          1          H       H      H    0      4,5-Br.sub.2                            1          H       H      H    1      4,5-Br.sub.2                            1          H       H      H    2      4,5-Br.sub.2                            1          H       H      H    3      4,5-Br.sub.2                            1          H       H      H    4      4,5-Br.sub.2                            1          H       H      H    5      4,5-Br.sub.2                            1          H       H      H    6      4,5-Br.sub.2                            1          H       H      H    0      2,4,5-Br.sub.3                          1          H       H      H    1      2,4,5-Br.sub.3                          1          H       H      H    2      2,4,5-Br.sub.3                          1          H       H      H    3      2,4,5-Br.sub.3                          1          H       H      H    4      2,4,5-Br.sub.3                          1          H       H      H    5      2,4,5-Br.sub.3                          1          H       H      H    6      2,4,5-Br.sub.3                          1          H       H      H    0      4,5-(CN).sub.2                          1          H       H      H    1      4,5-(CN).sub.2                          1          H       H      H    2      4,5-(CN).sub.2                          1          H       H      H    3      4,5-(CN).sub.2                          1          H       H      H    4      4,5-(CN).sub.2                          1          H       H      H    5      4,5-(CN).sub.2                          1          H       H      H    6      4,5-(CN).sub.2                          1          H       H      CH.sub.3                                                                           0      H                                       1          H       H      H    0      2-NO.sub.2                              1          H       H      H    1      2-NO.sub.2                              1          H       H      H    2      2-NO.sub.2                              1          H       H      H    3      2-NO.sub.2                              1          H       H      H    4      2-NO.sub.2                              1          H       H      H    5      2-NO.sub.2                              1          H       H      H    6      2-NO.sub.2                              4          H       H      H    0      H                                       4          H       H      H    1      H                                       4          H       H      H    2      H                                       5          H       H      H    0      4-CH.sub.3                              2          H       H      H    0      H                                       ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                         ##STR28##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       B       R.sup.5                                                                              R.sup.6                                                                             R.sup.7                                                                           p     (R.sup.8).sub.r                     ______________________________________                                        2          S       H      H     H   0     H                                   2          S       H      H     H   1     H                                   2          S       H      H     H   2     H                                   2          S       H      H     H   3     H                                   2          S       H      H     H   4     H                                   2          S       H      H     H   5     H                                   2          S       H      H     H   6     H                                   2          S       H      H     H   0     1-CH.sub.3                          2          S       H      H     H   1     1-CH.sub.3                          2          S       H      H     H   2     1-CH.sub.3                          2          S       H      H     H   3     1-CH.sub.3                          2          S       H      H     H   4     1-CH.sub.3                          2          S       H      H     H   5     1-CH.sub.3                          2          S       H      H     H   6     1-CH.sub.3                          ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                         ##STR29##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                        ______________________________________                                        4          H       H       H   0       3,6-Cl.sub.2                           4          H       H       H   1       3,6-Cl.sub.2                           4          H       H       H   2       3,6-Cl.sub.2                           4          H       H       H   3       3,6-Cl.sub.2                           4          H       H       H   4       3,6-Cl.sub.2                           4          H       H       H   5       3,6-Cl.sub.2                           4          H       H       H   6       3,6-Cl.sub.2                           ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                         ##STR30##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        3           H       H       H   0       H                                     3           H       H       H   1       H                                     3           H       H       H   2       H                                     3           H       H       H   3       H                                     3           H       H       H   4       H                                     3           H       H       H   5       H                                     3           H       H       H   6       H                                     ______________________________________                                    

                  TABLE 19                                                        ______________________________________                                         ##STR31##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        1           H       H       H   0       H                                     1           H       H       H   1       H                                     1           H       H       H   2       H                                     1           H       H       H   3       H                                     1           H       H       H   4       H                                     1           H       H       H   5       H                                     1           H       H       H   6       H                                     4           H       H       H   0       H                                     4           H       H       H   1       H                                     4           H       H       H   2       H                                     4           H       H       H   3       H                                     4           H       H       H   4       H                                     4           H       H       H   5       H                                     4           H       H       H   6       H                                     ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                         ##STR32##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       B       R.sup.5                                                                              R.sup.6                                                                             R.sup.7                                                                           p     (R.sup.8).sub.r                     ______________________________________                                        3          S       H      H     H   0     H                                   3          S       H      H     H   1     H                                   3          S       H      H     H   2     H                                   3          S       H      H     H   3     H                                   3          S       H      H     H   4     H                                   3          S       H      H     H   5     H                                   3          S       H      H     H   6     H                                   5          S       H      H     H   0     1-CH.sub.3                          5          S       H      H     H   1     1-CH.sub.3                          5          S       H      H     H   2     1-CH.sub.3                          5          S       H      H     H   3     1-CH.sub.3                          5          S       H      H     H   4     1-CH.sub.3                          5          S       H      H     H   5     1-CH.sub.3                          5          S       H      H     H   6     1-CH.sub.3                          ______________________________________                                    

                  TABLE 21                                                        ______________________________________                                         ##STR33##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        1           H       H       H   0       H                                     1           H       H       H   1       H                                     1           H       H       H   2       H                                     1           H       H       H   3       H                                     1           H       H       H   4       H                                     1           H       H       H   5       H                                     1           H       H       H   6       H                                     ______________________________________                                    

                  TABLE 22                                                        ______________________________________                                         ##STR34##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       B      R.sup.5 R.sup.6                                                                            R.sup.7                                                                           p     (R.sup.8).sub.r                      ______________________________________                                        5          S      H       H    H   0     1-CH.sub.3                           5          S      H       H    H   1     1-CH.sub.3                           5          S      H       H    H   2     1-CH.sub.3                           5          S      H       H    H   3     1-CH.sub.3                           5          S      H       H    H   4     1-CH.sub.3                           5          S      H       H    H   5     1-CH.sub.3                           5          S      H       H    H   6     1-CH.sub.3                           ______________________________________                                    

                  TABLE 23                                                        ______________________________________                                         ##STR35##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        R.sup.5 R.sup.6 R.sup.7                                                                           p       (R.sup.8).sub.r                       ______________________________________                                        4           H       H       H   0       H                                     4           H       H       H   1       H                                     4           H       H       H   2       H                                     4           H       H       H   3       H                                     4           H       H       H   4       H                                     4           H       H       H   5       H                                     4           H       H       H   6       H                                     4           H       H       H   0       6-CH.sub.3                            4           H       H       H   1       6-CH.sub.3                            4           H       H       H   2       6-CH.sub.3                            4           H       H       H   3       6-CH.sub.3                            4           H       H       H   4       6-CH.sub.3                            4           H       H       H   5       6-CH.sub.3                            4           H       H       H   6       6-CH.sub.3                            4           H       H       H   0       2,6-Cl.sub.2                          ______________________________________                                    

                  TABLE 24                                                        ______________________________________                                         ##STR36##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring     B       R.sup.5                                                                              R.sup.6                                                                            R.sup.7                                                                            p    (R.sup.8).sub.r                        ______________________________________                                        2        O       H      H    H    6    4-CH.sub.3                             4        O       H      H    H    0    2,6-(CH.sub.3).sub.2                   4        O       H      H    H    1    2,6-(CH.sub.3).sub.2                   4        O       H      H    H    2    2,6-(CH.sub.3).sub.2                   4        O       H      H    H    3    2,6-(CH.sub.3).sub.2                   4        O       H      H    H    4    2,6-(CH.sub.3).sub.2                   4        O       H      H    H    5    2,6-(CH.sub.3).sub.2                   4        O       H      H    H    6    2,6-(CH.sub.3).sub.2                   2        S       H      H    H    0    H                                      2        S       H      H    H    1    H                                      2        S       H      H    H    2    H                                      2        S       H      H    H    3    H                                      2        S       H      H    H    4    H                                      2        S       H      H    H    5    H                                      2        S       H      H    H    6    H                                      2        NH      H      H    H    1    H                                      2        NH      H      H    H    0    H                                      2        O       H      H    H    2    5-CF.sub.3                             2        O       H      H    H    3    5-CF.sub.3                             5        O       H      H    H    2    5-CF.sub.3                             5        O       H      H    H    3    5-CF.sub.3                             2        NH      H      H    H    2    H                                      2        NH      H      H    H    3    H                                      2        NH      H      H    H    4    H                                      3        NH      H      H    H    5    H                                      3        NH      H      H    H    6    H                                      3        S       H      H    H    0    4-CH.sub.3                             3        S       H      H    H    1    4-CH.sub.3                             3        S       H      H    H    2    4-CH.sub.3                             3        S       H      H    H    3    4-CH.sub.3                             3        S       H      H    H    4    4-CH.sub.3                             2        O       H      H    H    0    H                                      2        O       H      H    H    1    H                                      2        O       H      H    H    2    H                                      2        O       H      H    H    3    H                                      2        O       H      H    H    4    H                                      2        O       H      H    H    5    H                                      2        O       H      H    H    6    H                                      2        O       H      H    H    0    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    1    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    2    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    3    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    4    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    5    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    6    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    0    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    1    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    2    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    3    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    4    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    5    4,6-(CH.sub.3).sub.2                   2        NH      H      H    H    6    4,6-(CH.sub.3).sub.2                   2        O       H      H    H    0    4-CH.sub.3                             2        O       H      H    H    1    4-CH.sub.3                             2        O       H      H    H    2    4-CH.sub.3                             2        O       H      H    H    3    4-CH.sub.3                             2        O       H      H    H    4    4-CH.sub.3                             2        O       H      H    H    5    4-CH.sub.3                             2        S       H      H    H    5    4-CH.sub.3                             2        S       H      H    H    6    4-CH.sub.3                             2        NH      H      H    H    0    4-CH.sub.3                             2        NH      H      H    H    1    4-CH.sub.3                             2        NH      H      H    H    2    4-CH.sub.3                             2        NH      H      H    H    3    4-CH.sub.3                             2        NH      H      H    H    4    4-CH.sub.3                             2        NH      H      H    H    5    4-CH.sub.3                             2        NH      H      H    H    6    4-CH.sub.3                             2        S       H      H    H    0    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    1    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    2    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    3    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    4    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    5    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    0    4,6-Cl.sub.2                           2        S       H      H    H    6    4,6-(CH.sub.3).sub.2                   2        S       H      H    H    1    4,6-Cl.sub.2                           2        S       H      H    H    2    4,6-Cl.sub.2                           2        S       H      H    H    3    4,6-Cl.sub.2                           2        S       H      H    H    4    4,6-Cl.sub.2                           2        S       H      H    H    5    4,6-Cl.sub.2                           2        S       H      H    H    6    4,6-Cl.sub.2                           4        NH      H      H    H    0    H                                      4        NH      H      H    H    1    H                                      4        NH      H      H    H    2    H                                      4        NH      H      H    H    3    H                                      4        NH      H      H    H    4    H                                      4        NH      H      H    H    5    H                                      4        NH      H      H    H    6    H                                      2        NH      H      H    H    0    5-Br                                   2        NH      H      H    H    1    5-Br                                   2        NH      H      H    H    2    5-Br                                   2        NH      H      H    H    3    5-Br                                   2        NH      H      H    H    4    5-Br                                   2        NH      H      H    H    5    5-Br                                   2        NH      H      H    H    6    5-Br                                   4        NH      H      H    H    0    2,6-(CH.sub.3).sub.2                   4        NH      H      H    H    1    2,6-(CH.sub.3).sub.2                   4        NH      H      H    H    2    2,6-(CH.sub.3).sub.2                   4        NH      H      H    H    3    2,6-(CH.sub.3).sub.2                   4        NH      H      H    H    4    2,6-(CH.sub.3).sub.2                   4        NH      H      H    H    5    2,6-(CH.sub.3).sub.2                   4        NH      H      H    H    6    2,6-(CH.sub.3).sub.2                   2        NH      H      H    H    0    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    1    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    2    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    3    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    4    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    5    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    6    4-Cl, 6-CH.sub.3                       2        NH      H      H    H    0    4-OCH.sub.3, 6-CH.sub.3                2        NH      H      H    H    1    4-OCH.sub.3, 6-CH.sub.3                2        NH      H      H    H    2    4-OCH.sub.3, 6-CH.sub.3                2        NH      H      H    H    3    4-OCH.sub.3, 6-CH.sub.3                2        NH      H      H    H    4    4-OCH.sub.3, 6-CH.sub.3                2        NH      H      H    H    5    4-OCH.sub.3, 6-CH.sub.3                2        NH      H      H    H    6    4-OCH.sub.3, 6-CH.sub.3                2        O       H      H    H    0    4,6-(OCH.sub.3).sub.2                  2        O       H      H    H    1    4,6-(OCH.sub.3).sub.2                  2        O       H      H    H    2    4,6-(OCH.sub.3).sub.2                  2        O       H      H    H    3    4,6-(OCH.sub.3).sub.2                  2        O       H      H    H    4    4,6-(OCH.sub.3).sub.2                  2        O       H      H    H    5    4,6-(OCH.sub.3).sub.2                  2        O       H      H    H    6    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    0    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    1    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    2    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    4    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    3    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    2    5-CF.sub.3                             2        NH      H      H    H    3    5-CF.sub.3                             5        NH      H      H    H    2    5-CF.sub.3                             5        NH      H      H    H    3    5-CF.sub.3                             2        NH      H      H    H    5    4,6-(OCH.sub.3).sub.2                  2        NH      H      H    H    6    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    0    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    1    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    2    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    3    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    4    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    5    4,6-(OCH.sub.3).sub.2                  2        S       H      H    H    6    4,6-(OCH.sub.3).sub.2                  5        NH      H      H    H    0    4,6-Cl.sub.2                           5        NH      H      H    H    1    4,6-Cl.sub.2                           2        S       H      H    H    2    5-CF.sub.3                             2        S       H      H    H    3    5-CF.sub.3                             5        S       H      H    H    2    5-CF.sub.3                             5        S       H      H    H    3    5-CF.sub.3                             ______________________________________                                    

                  TABLE 25                                                        ______________________________________                                         ##STR37##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5                                                                              R.sup.6                                                                              R.sup.7                                                                            p    (R.sup.8 ).sub.r                           ______________________________________                                        2          H      H      H    0    H                                          2          H      H      H    1    H                                          2          H      H      H    2    H                                          2          H      H      H    3    H                                          2          H      H      H    4    H                                          2          H      H      H    5    H                                          2          H      H      H    6    5-CH.sub.3                                 2          H      H      H    0    5-CH.sub.3                                 2          H      H      H    1    5-CH.sub.3                                 2          H      H      H    2    5-CH.sub.3                                 2          H      H      H    3    5-CH.sub.3                                 2          H      H      H    4    5-CH.sub.3                                 2          H      H      H    5    5-CH.sub.3                                 2          H      H      H    6    5-CH.sub.3                                 2          H      H      H    0    6-CH.sub.3                                 2          H      H      H    1    6-CH.sub.3                                 2          H      H      H    2    6-CH.sub.3                                 2          H      H      H    3    6-CH.sub.3                                 2          H      H      H    4    6-CH.sub.3                                 2          H      H      H    5    6-CH.sub.3                                 2          H      H      H    6    6-CH.sub.3                                 2          H      H      H    0    3-CH.sub.3                                 2          H      H      H    1    3-CH.sub.3                                 2          H      H      H    2    3-CH.sub.3                                 2          H      H      H    3    3-CH.sub.3                                 2          H      H      H    4    3-CH.sub.3                                 2          H      H      H    5    3-CH.sub.3                                 2          H      H      H    6    3-CH.sub.3                                 2          H      H      H    0    5-CH.sub.3                                 2          H      H      H    1    5-CH.sub.3                                 2          H      H      H    2    5-CH.sub.3                                 2          H      H      H    3    5-CH.sub.3                                 2          H      H      H    4    5-CH.sub.3                                 2          H      H      H    5    5-CH.sub.3                                 2          H      H      H    6    5-CH.sub.3                                 2          H      H      H    0    3-OCH.sub.3                                2          H      H      H    1    3-OCH.sub.3                                2          H      H      H    2    3-OCH.sub.3                                2          H      H      H    3    3-OCH.sub.3                                2          H      H      H    4    3-OCH.sub.3                                2          H      H      H    5    3-OCH.sub.3                                2          H      H      H    6    3-OCH.sub.3                                2          H      H      H    0    6-OCH.sub.2 CH.sub.2 CH.sub.3              2          H      H      H    1    6-OCH.sub.2 CH.sub.2 CH.sub.3              2          H      H      H    2    6-OCH.sub.2 CH.sub.2 CH.sub.3              2          H      H      H    3    6-OCH.sub.2 CH.sub.2 CH.sub.3              2          H      H      H    4    6-OCH.sub.2 CH.sub.2 CH.sub.3              2          H      H      H    5    6-OCH.sub.2 CH.sub.2 CH.sub.3              2          H      H      H    6    6-OCH.sub.2 CH.sub.2 CH.sub.3              ______________________________________                                    

                  TABLE 26                                                        ______________________________________                                         ##STR38##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       B       R.sup.5                                                                              R.sup.6                                                                             R.sup.7                                                                            p     (R.sup.8).sub.r                    ______________________________________                                        2          O       H      H     H    0     H                                  2          O       H      H     H    1     H                                  2          O       H      H     H    2     H                                  2          O       H      H     H    3     H                                  2          O       H      H     H    4     H                                  2          O       H      H     H    5     H                                  2          O       H      H     H    6     H                                  2          NH      H      H     H    0     H                                  2          NH      H      H     H    1     H                                  2          NH      H      H     H    2     H                                  2          NH      H      H     H    3     H                                  2          NH      H      H     H    4     H                                  2          NH      H      H     H    5     H                                  2          NH      H      H     H    6     H                                  2          S       H      H     H    0     H                                  2          S       H      H     H    1     H                                  2          S       H      H     H    2     H                                  2          S       H      H     H    3     H                                  2          S       H      H     H    4     H                                  2          S       H      H     H    5     H                                  2          S       H      H     H    6     H                                  2          O       H      H     H    0     6-Cl                               2          O       H      H     H    1     6-Cl                               2          O       H      H     H    2     6-Cl                               2          O       H      H     H    3     6-Cl                               2          O       H      H     H    4     6-Cl                               2          O       H      H     H    5     6-Cl                               2          O       H      H     H    6     6-Cl                               2          NH      H      H     H    0     6-Cl                               2          NH      H      H     H    1     6-Cl                               2          NH      H      H     H    2     6-Cl                               2          NH      H      H     H    3     6-Cl                               2          NH      H      H     H    4     6-Cl                               2          NH      H      H     H    5     6-Cl                               2          NH      H      H     H    6     6-Cl                               2          S       H      H     H    0     6-Cl                               2          S       H      H     H    1     6-Cl                               2          S       H      H     H    2     6-Cl                               2          S       H      H     H    3     6-Cl                               2          S       H      H     H    4     6-Cl                               2          S       H      H     H    5     6-Cl                               2          S       H      H     H    6     6-Cl                               ______________________________________                                    

                  TABLE 27                                                        ______________________________________                                         ##STR39##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       B       R.sup.5                                                                              R.sup.6                                                                             R.sup.7                                                                            p     (R.sup.8).sub.r                    ______________________________________                                        3          NH      H      H     H    0     H                                  3          NH      H      H     H    1     H                                  3          NH      H      H     H    2     H                                  3          NH      H      H     H    3     H                                  3          NH      H      H     H    4     H                                  3          NH      H      H     H    5     H                                  3          NH      H      H     H    6     H                                  ______________________________________                                    

                  TABLE 28                                                        ______________________________________                                         ##STR40##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring     B       R.sup.5                                                                              R.sup.6                                                                            R.sup.7                                                                            p    (R.sup.8).sub.r                        ______________________________________                                        2        O       H      H    H    0    4,6-Cl.sub.2                           2        O       H      H    H    1    4,6-Cl.sub.2                           2        O       H      H    H    2    4,6-Cl.sub.2                           2        O       H      H    H    3    4,6-Cl.sub.2                           2        O       H      H    H    4    4,6-Cl.sub.2                           2        O       H      H    H    5    4,6-Cl.sub.2                           2        O       H      H    H    6    4,6-Cl.sub.2                           2        S       H      H    H    0    4,6-Cl.sub.2                           2        S       H      H    H    1    4,6-Cl.sub.2                           2        S       H      H    H    2    4,6-Cl.sub.2                           2        S       H      H    H    3    4,6-Cl.sub.2                           2        S       H      H    H    4    4,6-Cl.sub.2                           2        S       H      H    H    5    4,6-Cl.sub.2                           2        S       H      H    H    6    4,6-Cl.sub.2                           2        NH      H      H    H    0    4,6-Cl.sub.2                           2        NH      H      H    H    2    4,6-Cl.sub.2                           2        NH      H      H    H    1    4,6-Cl.sub.2                           2        NH      H      H    H    3    4,6-Cl.sub.2                           2        NH      H      H    H    4    4,6-Cl.sub.2                           2        NH      H      H    H    5    4,6-Cl.sub.2                           2        NH      H      H    H    6    4,6-Cl.sub.2                           2        O       H      H    H    0    4-Cl, 6-OCH.sub.3                      2        O       H      H    H    1    4-Cl, 6-OCH.sub.3                      2        O       H      H    H    2    4-Cl, 6-OCH.sub.3                      2        O       H      H    H    3    4-Cl, 6-OCH.sub.3                      2        O       H      H    H    4    4-Cl, 6-OCH.sub.3                      2        O       H      H    H    5    4-Cl, 6-OCH.sub.3                      2        O       H      H    H    6    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    1    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    0    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    2    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    3    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    4    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    5    4-Cl, 6-OCH.sub.3                      2        NH      H      H    H    6    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    0    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    1    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    2    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    3    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    4    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    5    4-Cl, 6-OCH.sub.3                      2        S       H      H    H    6    4-Cl, 6-OCH.sub.3                      ______________________________________                                    

                  TABLE 29                                                        ______________________________________                                         ##STR41##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring       R.sup.5                                                                             R.sup.6  R.sup.7                                                                            p     (R.sup.8).sub.r                          ______________________________________                                        3          H     H        H    0     H                                        3          H     H        H    0     6-Cl                                     3          H     H        H    0     6-Br                                     3          H     H        H    0     6-I                                      3          H     H        H    0     6-CH.sub.3                               3          H     H        H    0     6-CF.sub.3                               3          H     H        CH.sub.3                                                                           0     H                                        3          H     H        H    0     2-CH.sub.3                               3          H     H        H    0     4-(CH.sub.2).sub.3 CH.sub.3              3          H     H        H    0     2-Cl                                     3          H     H        H    0     4-Br                                     3          H     H        H    0     2,6-Cl.sub.2                             3          H     H        H    0     2-Cl, 6-CH.sub.3                         3          H     H        H    0     5,6-Cl.sub.2                             3          H     H        H    0     2,6-(OCH.sub.3).sub.2                    3          H     H        H    0     2-SCH.sub.3                              3          H     H        H    0     5-CH.sub.3                               3          H     H        H    1     H                                        3          H     H        H    2     H                                        3          H     H        H    3     H                                        3          H     H        H    4     H                                        3          H     H        H    5     H                                        3          H     H        H    6     H                                        3          H     H        H    1     5-CH.sub.3                               3          H     H        H    2     5-CH.sub.3                               3          H     H        H    3     5-CH.sub.3                               3          H     H        H    4     5-CH.sub.3                               3          H     H        H    5     5-CH.sub.3                               3          H     H        H    6     5-CH.sub.3                               3          H     H        CH.sub.3                                                                           1     H                                        3          H     H        CH.sub.3                                                                           2     H                                        3          H     H        CH.sub.3                                                                           4     H                                        3          H     H        CH.sub.3                                                                           5     H                                        3          H     H        CH.sub.3                                                                           3     H                                        3          H     H        CH.sub.3                                                                           6     H                                        3          H     H        CH.sub.3                                                                           1     2-CH.sub.3                               3          H     H        CH.sub.3                                                                           2     2-CH.sub.3                               3          H     H        CH.sub.3                                                                           3     2-CH.sub.3                               3          H     H        CH.sub.3                                                                           4     2-CH.sub.3                               3          H     H        CH.sub.3                                                                           5     2-CH.sub.3                               3          H     H        CH.sub.3                                                                           6     2-CH.sub.3                               3          H     H        CH.sub.3                                                                           1     6-CH.sub.3                               3          H     H        CH.sub.3                                                                           2     6-CH.sub.3                               3          H     H        CH.sub.3                                                                           3     6-CH.sub.3                               3          H     H        H    4     6-CH.sub.3                               3          H     H        H    6     6-CH.sub.3                               3          H     H        H    5     6-CH.sub.3                               3          H     H        H    1     6-Cl                                     3          H     H        H    2     6-Cl                                     3          H     H        H    3     6-Cl                                     3          H     H        H    4     6-Cl                                     3          H     H        H    5     6-Cl                                     3          H     H        H    6     6-Cl                                     3          H     H        H    1     6-Br                                     3          H     H        H    2     6-Br                                     3          H     H        H    3     6-Br                                     3          H     H        H    4     6-Br                                     3          H     H        H    5     6-Br                                     3          H     H        H    6     6-Br                                     3          H     H        H    1     6-I                                      3          H     H        H    2     6-I                                      3          H     H        H    3     6-I                                      3          H     H        H    4     6-I                                      3          H     H        H    5     6-I                                      3          H     H        H    6     6-I                                      3          H     H        H    1     6-CF.sub.3                               3          H     H        H    2     6-CF.sub.3                               3          H     H        H    3     6-CF.sub.3                               3          H     H        H    4     6-CF.sub.3                               3          H     H        H    5     6-CF.sub.3                               3          H     H        H    6     6-CF.sub.3                               3          H     H        H    1     2-Cl                                     3          H     H        H    2     2-Cl                                     3          H     H        H    3     2-Cl                                     3          H     H        H    4     2-Cl                                     3          H     H        H    5     2-Cl                                     3          H     H        H    6     2-Cl                                     3          H     H        H    1     5-Br                                     3          H     H        H    2     5-Br                                     3          H     H        H    3     5-Br                                     3          H     H        H    4     5-Br                                     3          H     H        H    5     5-Br                                     3          H     H        H    6     5-Br                                     3          H     H        H    1     2-Cl, 6-CH.sub.3                         3          H     H        H    2     2-Cl, 6-CH.sub.3                         3          H     H        H    4     2-Cl, 6-CH.sub.3                         3          H     H        H    3     2-Cl, 6-CH.sub.3                         3          H     H        H    5     2-Cl, 6-CH.sub.3                         3          H     H        H    6     2-Cl, 6-CH.sub.3                         3          H     H        H    1     2,6-Cl.sub.2                             3          H     H        H    2     2,6-Cl.sub.2                             3          H     H        H    3     2,6-Cl.sub.2                             3          H     H        H    4     2,6-Cl.sub.2                             3          H     H        H    5     2,6-Cl.sub.2                             3          H     H        H    6     2,6-Cl.sub.2                             3          H     H        H    1     5,6-Cl.sub.2                             3          H     H        H    2     5,6-Cl.sub.2                             3          H     H        H    3     5,6-Cl.sub.2                             3          H     H        H    4     5,6-Cl.sub.2                             3          H     H        H    5     5,6-Cl.sub.2                             3          H     H        H    6     5,6-Cl.sub.2                             3          H     H        H    1     5,6-(OCH.sub.3).sub.2                    3          H     H        H    2     5,6-(OCH.sub.3).sub.2                    3          H     H        H    3     5,6-(OCH.sub.3).sub.2                    3          H     H        H    4     5,6-(OCH.sub.3).sub.2                    3          H     H        H    5     5,6-(OCH.sub.3).sub.2                    3          H     H        H    6     5,6-(OCH.sub.3).sub.2                    3          H     H        H    1     2-SCH.sub.3                              3          H     H        H    2     2-SCH.sub.3                              3          H     H        H    3     2-SCH.sub.3                              3          H     H        H    4     2-SCH.sub.3                              3          H     H        H    5     2-SCH.sub.3                              3          H     H        H    6     2-SCH.sub.3                              2          H     H        H    0     H                                        2          H     H        H    1     H                                        2          H     H        H    2     H                                        2          H     H        H    3     H                                        2          H     H        H    4     H                                        2          H     H        H    5     H                                        2          H     H        H    6     H                                        2          H     H        H    0     6-CH.sub.3                               2          H     H        H    1     6-CH.sub.3                               2          H     H        H    2     6-CH.sub.3                               2          H     H        H    3     6-CH.sub.3                               2          H     H        H    4     6-CH.sub.3                               2          H     H        H    5     6-CH.sub.3                               2          H     H        H    6     6-CH.sub.3                               2          H     H        H    0     6-Cl                                     2          H     H        H    1     6-Cl                                     2          H     H        H    2     6-Cl                                     2          H     H        H    3     6-Cl                                     2          H     H        H    4     6-Cl                                     2          H     H        H    5     6-Cl                                     2          H     H        H    6     6-Cl                                     2          H     H        H    0     5-CF.sub.3                               2          H     H        H    1     5-CF.sub.3                               2          H     H        H    2     5-CF.sub.3                               2          H     H        H    3     5-CF.sub.3                               2          H     H        H    4     5-CF.sub.3                               2          H     H        H    5     5-CF.sub.3                               2          H     H        H    0     5-Cl                                     2          H     H        H    6     5-CF.sub.3                               2          H     H        H    1     5-Cl                                     2          H     H        H    2     5-Cl                                     2          H     H        H    3     5-Cl                                     2          H     H        H    4     5-Cl                                     2          H     H        H    5     5-Cl                                     2          H     H        H    6     5-Cl                                     2          H     H        H    0     3-Cl                                     2          H     H        H    1     3-Cl                                     2          H     H        H    2     3-Cl                                     2          H     H        H    3     3-Cl                                     2          H     H        H    4     3-Cl                                     2          H     H        H    5     3-Cl                                     2          H     H        H    6     3-Cl                                     2          H     H        H    0     6-F                                      2          H     H        H    1     6-F                                      2          H     H        H    2     6-F                                      2          H     H        H    3     6-F                                      2          H     H        H    4     6-F                                      2          H     H        H    5     6-F                                      2          H     H        H    6     6-F                                      2          H     H        H    0     6-Br                                     2          H     H        H    1     6-Br                                     2          H     H        H    2     6-Br                                     2          H     H        H    3     6-Br                                     2          H     H        H    4     6-Br                                     2          H     H        H    5     6-Br                                     2          H     H        H    6     6-Br                                     3          H     H        H    0     6-Cl                                     3          H     H        H    1     6-Cl                                     3          H     H        H    2     6-Cl                                     3          H     H        H    3     6-Cl                                     3          H     H        H    4     6-Cl                                     3          H     H        H    5     6-Cl                                     3          H     H        H    6     6-Cl                                     3          H     H        H    0     5-Cl                                     3          H     H        H    1     5-Cl                                     3          H     H        H    2     5-Cl                                     2          H     H        H    3     5-Cl                                     2          H     H        H    4     5-Cl                                     2          H     H        H    5     5-Cl                                     2          H     H        H    6     5-Cl                                     2          H     H        H    0     5-Br                                     2          H     H        H    1     5-Br                                     2          H     H        H    2     5-Br                                     2          H     H        H    3     5-Br                                     2          H     H        H    4     5-Br                                     2          H     H        H    5     5-Br                                     2          H     H        H    6     5-Br                                     2          H     H        H    0     3,5-(CF.sub.3).sub.2                     2          H     H        H    1     3,5-(CF.sub.3).sub.2                     2          H     H        H    2     3,5-(CF.sub.3).sub.2                     2          H     H        H    3     3,5-(CF.sub.3).sub.2                     2          H     H        H    4     3,5-(CF.sub.3).sub.2                     2          H     H        H    5     3,5-(CF.sub.3).sub.2                     2          H     H        H    6     3,5-(CF.sub.3).sub.2                     2          H     H        H    0     4,5-(CF.sub.3).sub.2                     2          H     H        H    1     4,5-(CF.sub.3).sub.2                     2          H     H        H    2     4,5-(CF.sub.3).sub.2                     2          H     H        H    3     4,5-(CF.sub.3).sub.2                     2          H     H        H    4     4,5-(CF.sub.3).sub.2                     2          H     H        H    5     4,5-(CF.sub.3).sub.2                     2          H     H        H    6     4,5-(CF.sub.3).sub.2                     2          H     H        H    0     3,5-Cl.sub.2                             2          H     H        H    1     3,5-Cl.sub.2                             2          H     H        H    2     3,5-Cl.sub.2                             2          H     H        H    3     3,5-Cl.sub.2                             2          H     H        H    4     3,5-Cl.sub.2                             2          H     H        H    5     3,5-Cl.sub.2                             2          H     H        H    6     3,5-Cl.sub.2                             2          H     H        H    0     3-Cl, 5-CF.sub.3                         2          H     H        H    1     3-Cl, 5-CF.sub.3                         2          H     H        H    2     3-Cl, 5-CF.sub.3                         2          H     H        H    3     3-Cl, 5-CF.sub.3                         2          H     H        H    4     3-Cl, 5-CF.sub.3                         2          H     H        H    5     3-Cl, 5-CF.sub.3                         2          H     H        H    6     3-Cl, 5-CF.sub.3                         2          H     H        H    0     3,5,6-F.sub.3                            2          H     H        H    0     3,5,6-F.sub.3, 4CH.sub.3                 2          H     H        H    0     5-CN, 6-Cl                               4          H     H        H    0     H                                        4          H     H        H    1     H                                        4          H     H        H    2     H                                        4          H     H        H    3     H                                        4          H     H        H    4     H                                        4          H     H        H    5     H                                        4          H     H        H    6     H                                        4          H     H        H    0     2,3,5,6-F.sub.4                          4          H     H        CH.sub.3                                                                           0     H                                        4          H     H        CH.sub.3                                                                           1     H                                        4          H     H        CH.sub.3                                                                           2     H                                        4          H     H        CH.sub.3                                                                           3     H                                        4          H     H        CH.sub.3                                                                           4     H                                        4          H     H        CH.sub.3                                                                           5     H                                        4          H     H        CH.sub.3                                                                           6     H                                        2          H     H        CH.sub.3                                                                           0     H                                        2          H     H        CH.sub.3                                                                           1     H                                        2          H     H        CH.sub.3                                                                           2     H                                        2          H     H        CH.sub.3                                                                           3     H                                        2          H     H        CH.sub.3                                                                           4     H                                        2          H     H        CH.sub.3                                                                           5     H                                        2          H     H        CH.sub.3                                                                           6     H                                        ______________________________________                                    

                  TABLE 30                                                        ______________________________________                                         ##STR42##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring    B          R.sup.5                                                                             R.sup.6                                                                            R.sup.7                                                                            p    (R.sup.8).sub.r                       ______________________________________                                        2       O          H     H    H    0    H                                     2       O          H     H    H    1    H                                     2       O          H     H    H    2    H                                     2       O          H     H    H    3    H                                     2       O          H     H    H    4    H                                     2       O          H     H    H    5    H                                     2       O          H     H    H    6    H                                     2       NH         H     H    H    0    H                                     2       NH         H     H    H    1    H                                     2       NH         H     H    H    2    H                                     2       NH         H     H    H    3    H                                     2       NH         H     H    H    4    H                                     2       NH         H     H    H    5    H                                     2       NH         H     H    H    6    H                                     2       S          H     H    H    0    H                                     2       S          H     H    H    1    H                                     2       S          H     H    H    2    H                                     2       S          H     H    H    3    H                                     2       S          H     H    H    4    H                                     2       S          H     H    H    5    H                                     2       S          H     H    H    6    H                                     2       O          H     H    H    0    4-CH.sub.3                            2       O          H     H    H    1    4-CH.sub.3                            2       O          H     H    H    2    4-CH.sub.3                            2       O          H     H    H    3    4-CH.sub.3                            2       O          H     H    H    4    4-CH.sub.3                            2       O          H     H    H    5    4-CH.sub.3                            2       O          H     H    H    6    4-CH.sub.3                            2       NH         H     H    H    0    4-CH.sub.3                            2       NH         H     H    H    1    4-CH.sub.3                            2       NH         H     H    H    2    4-CH.sub.3                            2       NH         H     H    H    3    4-CH.sub.3                            2       NH         H     H    H    4    4-CH.sub.3                            2       NH         H     H    H    5    4-CH.sub.3                            2       NH         H     H    H    6    4-CH.sub.3                            2       S          H     H    H    0    4-CH.sub.3                            2       S          H     H    H    1    4-CH.sub.3                            2       S          H     H    H    2    4-CH.sub.3                            2       S          H     H    H    3    4-CH.sub.3                            2       S          H     H    H    4    4-CH.sub.3                            2       S          H     H    H    5    4-CH.sub.3                            2       S          H     H    H    6    4-CH.sub.3                            2       O          H     H    H    0    6-CH.sub.3                            2       O          H     H    H    1    6-CH.sub.3                            2       O          H     H    H    2    6-CH.sub.3                            2       O          H     H    H    3    6-CH.sub.3                            2       O          H     H    H    4    6-CH.sub.3                            2       O          H     H    H    5    6-CH.sub.3                            2       O          H     H    H    6    6-CH.sub.3                            2       NH         H     H    H    0    6-CH.sub.3                            2       NH         H     H    H    1    6-CH.sub.3                            2       NH         H     H    H    2    6-CH.sub.3                            2       NH         H     H    H    3    6-CH.sub.3                            2       NH         H     H    H    4    6-CH.sub.3                            2       COO        H     H    H    1    H                                     2       COO        H     H    H    2    H                                     2       COO        H     H    H    3    H                                     3       COO        H     H    H    1    H                                     3       COO        H     H    H    2    H                                     3       COO        H     H    H    3    H                                     4       COO        H     H    H    1    H                                     4       COO        H     H    H    2    H                                     4       COO        H     H    H    3    H                                     2       COO        H     H    H    2    3-Cl, 5-CF.sub.3                      2       COO        H     H    H    3    3-Cl, 5-CF.sub.3                      2       COO        H     H    H    2    5-CF.sub.3                            2       COO        H     H    H    3    5-CF.sub.3                            3       COO        H     H    H    2    6-CF.sub.3                            3       COO        H     H    H    3    6-CF.sub.3                            3       COO        H     H    H    2    6-CH.sub.3                            3       COO        H     H    H    3    6-CH.sub.3                            3       COO        H     H    H    2    6-Cl                                  3       COO        H     H    H    3    6-Cl                                  3       COO        H     H    H    2    6-Br                                  3       COO        H     H    H    3    6-Br                                  3       COO        H     H    H    2    6-I                                   3       COO        H     H    H    3    6-I                                   2       NH         H     H    H    5    6-CH.sub.3                            2       NH         H     H    H    6    6-CH.sub.3                            2       S          H     H    H    0    6-CH.sub.3                            2       S          H     H    H    1    6-CH.sub.3                            2       S          H     H    H    2    6-CH.sub.3                            2       S          H     H    H    3    6-CH.sub.3                            2       S          H     H    H    4    6-CH.sub.3                            2       S          H     H    H    5    6-CH.sub.3                            2       S          H     H    H    6    6-CH.sub.3                            2       O          H     H    H    0    6-Cl                                  2       O          H     H    H    1    6-Cl                                  2       O          H     H    H    2    6-Cl                                  2       O          H     H    H    3    6-Cl                                  2       O          H     H    H    4    6-Cl                                  2       O          H     H    H    5    6-Cl                                  2       O          H     H    H    6    6-Cl                                  2       S          H     H    H    0    6-Cl                                  2       S          H     H    H    1    6-Cl                                  2       S          H     H    H    2    6-Cl                                  2       S          H     H    H    3    6-Cl                                  2       S          H     H    H    4    6-Cl                                  2       S          H     H    H    5    6-Cl                                  2       S          H     H    H    6    6-Cl                                  2       NH         H     H    H    0    6-Cl                                  2       NH         H     H    H    1    6-Cl                                  2       NH         H     H    H    2    6-Cl                                  2       NH         H     H    H    3    6-Cl                                  2       NH         H     H    H    4    6-Cl                                  2       NH         H     H    H    5    6-Cl                                  2       NH         H     H    H    6    6-Cl                                  2       O          H     H    H    0    5-Cl                                  2       O          H     H    H    1    5-Cl                                  2       O          H     H    H    2    5-Cl                                  2       O          H     H    H    3    5-Cl                                  2       O          H     H    H    4    5-Cl                                  2       O          H     H    H    5    5-Cl                                  2       O          H     H    H    6    5-Cl                                  2       NH         H     H    H    0    5-Cl                                  2       NH         H     H    H    1    5-Cl                                  2       NH         H     H    H    2    5-Cl                                  2       NH         H     H    H    3    5-Cl                                  2       NH         H     H    H    4    5-Cl                                  2       NH         H     H    H    5    5-Cl                                  2       NH         H     H    H    6    5-Cl                                  2       S          H     H    H    0    5-Cl                                  2       S          H     H    H    1    5-Cl                                  2       S          H     H    H    2    5-Cl                                  2       S          H     H    H    3    5-Cl                                  2       S          H     H    H    4    5-Cl                                  2       S          H     H    H    5    5-Cl                                  2       S          H     H    H    6    5-Cl                                  2       N--CH.sub.3                                                                              H     H    H    0    5-Cl                                  2       N--CH.sub.3                                                                              H     H    H    1    5-Cl                                  2       N--CH.sub.3                                                                              H     H    H    2    5-Cl                                  2       N--CH.sub.3                                                                              H     H    H    3    H                                     2       N--CH.sub.3                                                                              H     H    H    4    H                                     2       N--CH.sub.3                                                                              H     H    H    5    H                                     2       N--CH.sub.3                                                                              H     H    H    6    H                                     2       NH         H     H    H    0    3-CH.sub.3                            2       NH         H     H    H    1    3-CH.sub.3                            2       NH         H     H    H    2    3-CH.sub.3                            2       NH         H     H    H    3    3-CH.sub.3                            2       NH         H     H    H    4    3-CH.sub.3                            2       NH         H     H    H    5    3-CH.sub.3                            2       NH         H     H    H    6    3-CH.sub.3                            2       S          H     H    H    0    3-CH.sub.3                            2       S          H     H    H    1    3-CH.sub.3                            2       S          H     H    H    2    3-CH.sub.3                            2       S          H     H    H    3    3-CH.sub.3                            2       S          H     H    H    4    3-CH.sub.3                            2       S          H     H    H    5    3-CH.sub.3                            2       S          H     H    H    6    3-CH.sub.3                            2       O          H     H    H    0    3-CH.sub.3                            2       O          H     H    H    1    3-CH.sub.3                            2       O          H     H    H    2    3-CH.sub.3                            2       O          H     H    H    3    3-CH.sub.3                            2       O          H     H    H    4    3-CH.sub.3                            2       O          H     H    H    5    3-CH.sub.3                            2       O          H     H    H    6    3-CH.sub.3                            2       NH         H     H    H    0    5-CH.sub.3                            2       NH         H     H    H    1    5-CH.sub.3                            2       NH         H     H    H    2    5-CH.sub.3                            2       NH         H     H    H    3    5-CH.sub.3                            2       NH         H     H    H    4    5-CH.sub.3                            2       NH         H     H    H    5    5-CH.sub.3                            2       NH         H     H    H    6    5-CH.sub.3                            2       O          H     H    H    0    5-CH.sub.3                            2       O          H     H    H    1    5-CH.sub.3                            2       O          H     H    H    2    5-CH.sub.3                            2       O          H     H    H    3    5-CH.sub.3                            2       O          H     H    H    4    5-CH.sub.3                            2       O          H     H    H    5    5-CH.sub.3                            2       O          H     H    H    6    5-CH.sub.3                            2       S          H     H    H    0    5-CH.sub.3                            2       S          H     H    H    1    5-CH.sub.3                            2       S          H     H    H    2    5-CH.sub.3                            2       S          H     H    H    3    5-CH.sub.3                            2       S          H     H    H    4    5-CH.sub.3                            2       S          H     H    H    5    5-CH.sub.3                            2       S          H     H    H    6    5-CH.sub.3                            2       NH         H     H    H    0    5-Br                                  2       NH         H     H    H    1    5-Br                                  2       NH         H     H    H    2    5-Br                                  2       NH         H     H    H    3    5-Br                                  2       NH         H     H    H    4    5-Br                                  2       NH         H     H    H    5    5-Br                                  2       NH         H     H    H    6    5-Br                                  2       O          H     H    H    0    5-Br                                  2       O          H     H    H    1    5-Br                                  2       O          H     H    H    2    5-Br                                  2       O          H     H    H    3    5-Br                                  2       O          H     H    H    4    5-Br                                  2       O          H     H    H    5    5-Br                                  2       O          H     H    H    6    5-Br                                  2       S          H     H    H    0    5-Br                                  2       S          H     H    H    1    5-Br                                  2       S          H     H    H    2    5-Br                                  2       S          H     H    H    3    5-Br                                  2       S          H     H    H    4    5-Br                                  2       S          H     H    H    5    5-Br                                  2       S          H     H    H    6    5-Br                                  2       S          H     H    H    0    5-Br                                  2       S          H     H    H    1    5-Br                                  2       S          H     H    H    2    5-Br                                  2       S          H     H    H    3    5-Br                                  2       S          H     H    H    4    5-Br                                  2       S          H     H    H    5    5-Br                                  2       S          H     H    H    6    5-Br                                  2       NH         H     H    H    0    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    1    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    2    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    3    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    4    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    5    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    6    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    0    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    1    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    2    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    3    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    4    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    5    4,6-(CH.sub.3).sub.2                  2       O          H     H    H    6    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    0    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    1    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    2    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    3    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    4    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    5    4,6-(CH.sub.3).sub.2                  2       S          H     H    H    6    4,6-(CH.sub.3).sub.2                  2       NH         H     H    H    0    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    1    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    2    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    3    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    4    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    5    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    6    3-Cl, 5-CF.sub.3                      2       O          H     H    H    0    3-Cl, 5-CF.sub.3                      2       O          H     H    H    1    3-Cl, 5-CF.sub.3                      2       O          H     H    H    2    3-Cl, 5-CF.sub.3                      2       O          H     H    H    3    3-Cl, 5-CF.sub.3                      2       O          H     H    H    4    3-Cl, 5-CF.sub.3                      2       O          H     H    H    5    3-Cl, 5-CF.sub.3                      2       O          H     H    H    6    3-Cl, 5-CF.sub.3                      2       S          H     H    H    0    3-Cl, 5-CF.sub.3                      2       S          H     H    H    1    3-Cl, 5-CF.sub.3                      2       S          H     H    H    2    3-Cl, 5-CF.sub.3                      2       S          H     H    H    3    3-Cl, 5-CF.sub.3                      2       S          H     H    H    4    3-Cl, 5-CF.sub.3                      2       S          H     H    H    5    3-Cl, 5-CF.sub.3                      2       S          H     H    H    6    3-Cl, 5-CF.sub.3                      2       NH         H     H    H    0    5-NO.sub.2                            2       NH         H     H    H    1    5-NO.sub.2                            2       NH         H     H    H    0    3-Br, 5-CF.sub.3                      2       NH         H     H    H    1    3-Br, 5-CF.sub.3                      2       NH         H     H    H    2    3-Br, 5-CF.sub.3                      2       NH         H     H    H    3    3-Br, 5-CF.sub.3                      2       NH         H     H    H    4    3-Br, 5-CF.sub.3                      2       NH         H     H    H    5    3-Br, 5-CF.sub.3                      2       NH         H     H    H    6    3-Br, 5-CF.sub.3                      2       O          H     H    H    0    3-Br, 5-CF.sub.3                      2       O          H     H    H    1    3-Br, 5-CF.sub.3                      2       O          H     H    H    2    3-Br, 5-CF.sub.3                      2       O          H     H    H    3    3-Br, 5-CF.sub.3                      2       O          H     H    H    4    3-Br, 5-CF.sub.3                      2       O          H     H    H    5    3-Br, 5-CF.sub.3                      2       O          H     H    H    6    3-Br, 5-CF.sub.3                      2       S          H     H    H    0    3-Br, 5-CF.sub.3                      2       S          H     H    H    1    3-Br, 5-CF.sub.3                      2       S          H     H    H    2    3-Br, 5-CF.sub.3                      2       S          H     H    H    3    3-Br, 5-CF.sub.3                      2       S          H     H    H    4    3-Br, 5-CF.sub.3                      2       S          H     H    H    5    3-Br, 5-CF.sub.3                      2       S          H     H    H    6    3-Br, 5-CF.sub.3                      2       NH         H     H    H    0    3-F, 5-CF.sub.3                       2       NH         H     H    H    1    3-F, 5-CF.sub.3                       2       NH         H     H    H    2    3-F, 5-CF.sub.3                       2       NH         H     H    H    3    3-F, 5-CF.sub.3                       2       NH         H     H    H    4    3-F, 5-CF.sub.3                       2       NH         H     H    H    5    3-F, 5-CF.sub.3                       2       NH         H     H    H    6    3-F, 5-CF.sub.3                       2       O          H     H    H    0    3-F, 5-CF.sub.3                       2       O          H     H    H    1    3-F, 5-CF.sub.3                       2       O          H     H    H    2    3-F, 5-CF.sub.3                       2       O          H     H    H    3    3-F, 5-CF.sub.3                       2       O          H     H    H    4    3-F, 5-CF.sub.3                       2       O          H     H    H    5    3-F, 5-CF.sub.3                       2       O          H     H    H    6    3-F, 5-CF.sub.3                       2       S          H     H    H    0    3-F, 5-CF.sub.3                       2       S          H     H    H    1    3-F, 5-CF.sub.3                       2       S          H     H    H    2    3-F, 5-CF.sub.3                       2       S          H     H    H    3    3-F, 5-CF.sub.3                       2       S          H     H    H    4    3-F, 5-CF.sub.3                       2       S          H     H    H    5    3-F, 5-CF.sub.3                       2       S          H     H    H    6    3-F, 5-CF.sub.3                       2       NH         H     H    H    2    5-NO.sub.2                            2       NH         H     H    H    3    5-NO.sub.2                            2       NH         H     H    H    4    5-NO.sub.2                            2       NH         H     H    H    5    5-NO.sub.2                            2       NH         H     H    H    6    5-NO.sub.2                            2       O          H     H    H    0    5-NO.sub.2                            2       O          H     H    H    1    5-NO.sub.2                            2       O          H     H    H    2    5-NO.sub.2                            2       O          H     H    H    3    5-NO.sub.2                            2       O          H     H    H    4    5-NO.sub.2                            2       O          H     H    H    5    5-NO.sub.2                            2       O          H     H    H    6    5-NO.sub.2                            2       S          H     H    H    0    5-NO.sub.2                            2       S          H     H    H    1    5-NO.sub.2                            2       S          H     H    H    2    5-NO.sub.2                            2       S          H     H    H    3    5-NO.sub.2                            2       S          H     H    H    4    5-NO.sub.2                            2       S          H     H    H    5    5-NO.sub.2                            2       S          H     H    H    6    5-NO.sub.2                            2       NH         H     H    H    0    3-NO.sub.2, 5-Br                      2       NH         H     H    H    1    3-NO.sub.2, 5-Br                      2       NH         H     H    H    2    3-NO.sub.2, 5-Br                      2       NH         H     H    H    3    3-NO.sub.2, 5-Br                      2       NH         H     H    H    4    3-NO.sub.2, 5-Br                      2       NH         H     H    H    5    3-NO.sub.2, 5-Br                      2       NH         H     H    H    6    3-NO.sub.2, 5-Br                      2       O          H     H    H    0    3-NO.sub.2, 5-Br                      2       O          H     H    H    1    3-NO.sub.2, 5-Br                      2       O          H     H    H    2    3-NO.sub.2, 5-Br                      2       O          H     H    H    3    3-NO.sub.2, 5-Br                      2       O          H     H    H    4    3-NO.sub.2, 5-Br                      2       O          H     H    H    5    3-NO.sub.2, 5-Br                      2       O          H     H    H    6    3-NO.sub.2, 5-Br                      2       S          H     H    H    0    3-NO.sub.2, 5-Br                      2       S          H     H    H    1    3-NO.sub.2, 5-Br                      2       S          H     H    H    2    3-NO.sub.2, 5-Br                      2       S          H     H    H    3    3-NO.sub.2, 5-Br                      2       S          H     H    H    4    3-NO.sub.2, 5-Br                      2       S          H     H    H    5    3-NO.sub.2, 5-Br                      2       S          H     H    H    6    3-NO.sub.2, 5-Br                      2       NH         H     H    H    0    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    1    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    2    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    3    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    4    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    5    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    6    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    0    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    1    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    2    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    3    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    4    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    5    3-NO.sub.2, 4-CH.sub.3                2       S          H     H    H    6    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    0    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    1    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    2    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    3    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    4    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    5    3-NO.sub.2, 4-CH.sub.3                2       O          H     H    H    6    3-NO.sub.2, 4-CH.sub.3                2       NH         H     H    H    0    4-CH.sub.3, 5-NO.sub.2                2       NH         H     H    H    1    4-CH.sub.3, 5-NO.sub.2                2       NH         H     H    H    2    4-CH.sub.3, 5-NO.sub.2                2       NH         H     H    H    3    4-CH.sub.3, 5-NO.sub.2                2       NH         H     H    H    4    4-CH.sub.3, 5-NO.sub.2                2       NH         H     H    H    5    4-CH.sub.3, 5-NO.sub.2                2       NH         H     H    H    6    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    0    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    1    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    2    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    0    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    1    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    2    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    3    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    4    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    5    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    6    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    0    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    1    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    2    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    3    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    4    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    5    3,5-(CF.sub.3).sub.2                  2       NH         H     H    H    6    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    0    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    1    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    2    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    3    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    4    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    5    3,5-(CF.sub.3).sub.2                  2       S          H     H    H    6    3,5-(CF.sub.3).sub.2                  2       O          H     H    H    0    5-CF.sub.3                            2       O          H     H    H    1    5-CF.sub.3                            2       O          H     H    H    2    5-CF.sub.3                            2       O          H     H    H    3    5-CF.sub.3                            2       O          H     H    H    4    5-CF.sub.3                            2       O          H     H    H    5    5-CF.sub.3                            2       O          H     H    H    6    5-CF.sub.3                            2       S          H     H    H    0    5-CF.sub.3                            2       S          H     H    H    1    5-CF.sub.3                            2       S          H     H    H    2    5-CF.sub.3                            2       S          H     H    H    3    5-CF.sub.3                            2       S          H     H    H    4    5-CF.sub.3                            2       S          H     H    H    5    5-CF.sub.3                            2       S          H     H    H    6    5-CF.sub.3                            2       NH         H     H    H    0    5-CF.sub.3                            2       NH         H     H    H    1    5-CF.sub.3                            2       NH         H     H    H    2    5-CF.sub.3                            2       NH         H     H    H    3    5-CF.sub.3                            2       NH         H     H    H    4    5-CF.sub.3                            2       NH         H     H    H    5    5-CF.sub.3                            2       NH         H     H    H    6    5-CF.sub.3                            2       NCH.sub.3  H     H    H    0    5-CF.sub.3                            2       NCH.sub.3  H     H    H    1    5-CF.sub.3                            2       NCH.sub.3  H     H    H    2    5-CF.sub.3                            2       NCH.sub.3  H     H    H    3    5-CF.sub.3                            2       NCH.sub.3  H     H    H    4    5-CF.sub.3                            2       N--CH.sub.2 CH.sub.3                                                                     H     H    H    0    5-CF.sub.3                            2       N--CH.sub.2 CH.sub.3                                                                     H     H    H    1    5-CF.sub.3                            2       N--CH.sub.2 CH.sub.3                                                                     H     H    H    2    5-CF.sub.3                            2       N--CH.sub.2 CH.sub.3                                                                     H     H    H    3    5-CF.sub.3                            2       N--CH.sub.2 CH.sub.3                                                                     H     H    H    4    5-CF.sub.3                            2       N--(CH.sub.2).sub.2 CH.sub.3                                                             H     H    H    0    5-CF.sub.3                            2       N--(CH.sub.2).sub.2 CH.sub.3                                                             H     H    H    1    5-CF.sub.3                            2       N--(CH.sub.2).sub.2 CH.sub.3                                                             H     H    H    2    5-CF.sub.3                            2       N--(CH.sub.2).sub.2 CH.sub.3                                                             H     H    H    3    5-CF.sub.3                            2       N--(CH.sub.2).sub.2 CH.sub.3                                                             H     H    H    4    5-CF.sub.3                            2       N--CH(CH.sub.3).sub.2                                                                    H     H    H    0    5-CF.sub.3                            2       N--CH(CH.sub.3).sub.2                                                                    H     H    H    1    5-CF.sub.3                            2       N--CH(CH.sub.3).sub.2                                                                    H     H    H    2    5-CF.sub.3                            2       N--CH(CH.sub.3).sub.2                                                                    H     H    H    3    5-CF.sub.3                            2       N--CH(CH.sub.3).sub.2                                                                    H     H    H    4    5-CF.sub.3                            2       O          H     H    H    3    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    4    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    5    4-CH.sub.3, 5-NO.sub.2                2       O          H     H    H    6    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    0    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    1    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    2    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    3    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    4    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    5    4-CH.sub.3, 5-NO.sub.2                2       S          H     H    H    6    4-CH.sub.3, 5-NO.sub.2                3       O          H     H    H    0    H                                     3       O          H     H    H    1    H                                     3       O          H     H    H    2    H                                     3       O          H     H    H    3    H                                     3       O          H     H    H    4    H                                     3       O          H     H    H    5    H                                     3       O          H     H    H    6    H                                     3       O          H     H    H    0    2-CH.sub.3                            3       O          H     H    H    1    2-CH.sub.3                            3       O          H     H    H    2    2-CH.sub.3                            3       O          H     H    H    3    2-CH.sub.3                            3       O          H     H    H    4    2-CH.sub.3                            3       O          H     H    H    5    2-CH.sub.3                            3       O          H     H    H    6    2-CH.sub.3                            3       O          H     H    H    0    6-CH.sub.3                            3       O          H     H    H    1    6-CH.sub.3                            3       O          H     H    H    2    6-CH.sub.3                            3       O          H     H    H    3    6-CH.sub.3                            3       O          H     H    H    4    6-CH.sub.3                            3       O          H     H    H    5    6-CH.sub.3                            3       O          H     H    H    6    6-CH.sub.3                            3       O          H     H    H    0    5-Cl                                  3       O          H     H    H    1    5-Cl                                  3       O          H     H    H    2    5-Cl                                  3       O          H     H    H    3    5-Cl                                  3       O          H     H    H    4    5-Cl                                  3       O          H     H    H    5    5-Cl                                  3       O          H     H    H    6    5-Cl                                  3       O          H     H    H    0    2-Cl                                  3       O          H     H    H    1    2-Cl                                  3       O          H     H    H    2    2-Cl                                  3       O          H     H    H    3    2-Cl                                  3       O          H     H    H    4    2-Cl                                  3       O          H     H    H    5    2-Cl                                  3       O          H     H    H    6    2-Cl                                  3       O          H     H    H    0    2-Br                                  3       O          H     H    H    1    2-Br                                  3       O          H     H    H    2    2-Br                                  3       O          H     H    H    3    2-Br                                  3       O          H     H    H    4    2-Br                                  3       O          H     H    H    5    2-Br                                  3       O          H     H    H    6    2-Br                                  3       O          H     H    H    0    2-I, 6-CH.sub.3                       3       O          H     H    H    1    2-I, 6-CH.sub.3                       3       O          H     H    H    2    2-I, 6-CH.sub.3                       3       O          H     H    H    3    2-I, 6-CH.sub.3                       3       O          H     H    H    4    2-I, 6-CH.sub.3                       3       O          H     H    H    5    2-I, 6-CH.sub.3                       3       O          H     H    H    6    2-I, 6-CH.sub.3                       3       NH         H     H    H    0    H                                     3       NH         H     H    H    1    H                                     3       NH         H     H    H    2    H                                     3       NH         H     H    H    3    H                                     3       NH         H     H    H    4    H                                     3       NH         H     H    H    5    H                                     3       NH         H     H    H    6    H                                     3       NH         H     H    H    0    2-Cl                                  3       NH         H     H    H    1    2-Cl                                  3       NH         H     H    H    2    2-Cl                                  3       NH         H     H    H    3    2-Cl                                  3       NH         H     H    H    4    2-Cl                                  3       NH         H     H    H    5    2-Cl                                  3       NH         H     H    H    6    2-Cl                                  3       NH         H     H    H    0    5-OCH.sub.3                           3       NH         H     H    H    1    5-OCH.sub.3                           3       NH         H     H    H    2    5-OCH.sub.3                           3       NH         H     H    H    3    5-OCH.sub.3                           3       NH         H     H    H    4    5-OCH.sub.3                           3       NH         H     H    H    5    5-OCH.sub.3                           3       NH         H     H    H    6    5-OCH.sub.3                           3       NH         H     H    H    0    2,6-(OCH.sub.3).sub.2                 3       NH         H     H    H    1    2,6-(OCH.sub.3).sub.2                 3       NH         H     H    H    2    2,6-(OCH.sub.3).sub.2                 3       NH         H     H    H    3    2,6-(OCH.sub.3).sub.2                 3       NH         H     H    H    4    2,6-(OCH.sub.3).sub.2                 3       NH         H     H    H    5    2,6-(OCH.sub.3).sub.2                 3       NH         H     H    H    6    2,6-(OCH.sub.3).sub.2                 4       S          H     H    H    0    H                                     4       S          H     H    H    1    H                                     4       S          H     H    H    2    H                                     4       S          H     H    H    3    H                                     4       S          H     H    H    4    H                                     4       S          H     H    H    5    H                                     4       S          H     H    H    6    H                                     4       NH         H     H    H    0    H                                     4       NH         H     H    H    1    H                                     4       NH         H     H    H    2    H                                     4       NH         H     H    H    3    H                                     4       NH         H     H    H    4    H                                     4       NH         H     H    H    5    H                                     4       NH         H     H    H    6    H                                     4       O          H     H    H    0    H                                     4       O          H     H    H    1    H                                     4       O          H     H    H    2    H                                     4       O          H     H    H    3    H                                     4       O          H     H    H    4    H                                     4       O          H     H    H    5    H                                     4       O          H     H    H    6    H                                     4       S          H     H    H    0    2,3,5,6-Cl.sub.4                      4       S          H     H    H    1    2,3,5,6-Cl.sub.4                      4       S          H     H    H    2    2,3,5,6-Cl.sub.4                      4       S          H     H    H    3    2,3,5,6-Cl.sub.4                      4       S          H     H    H    4    2,3,5,6-Cl.sub.4                      4       S          H     H    H    5    2,3,5,6-Cl.sub.4                      4       S          H     H    H    6    2,3,5,6-Cl.sub.4                      ______________________________________                                    

                  TABLE 31                                                        ______________________________________                                         ##STR43##                                                                     ##STR44##                                                                     ##STR45##                                                                     ##STR46##                                                                     ##STR47##                                                                     ##STR48##                                                                     ##STR49##                                                                     ##STR50##                                                                     ##STR51##                                                                    ______________________________________                                    

                  TABLE 32                                                        ______________________________________                                         ##STR52##                                                                     ##STR53##                                                                     ##STR54##                                                                     ##STR55##                                                                     ##STR56##                                                                     ##STR57##                                                                     ##STR58##                                                                     ##STR59##                                                                    ______________________________________                                    

                  TABLE 33                                                        ______________________________________                                         ##STR60##                                                                     ##STR61##                                                                     ##STR62##                                                                     ##STR63##                                                                     ##STR64##                                                                     ##STR65##                                                                     ##STR66##                                                                     ##STR67##                                                                    ______________________________________                                    

                  TABLE 34                                                        ______________________________________                                         ##STR68##                                                                     ##STR69##                                                                     ##STR70##                                                                     ##STR71##                                                                     ##STR72##                                                                     ##STR73##                                                                    ______________________________________                                    

In Tables 31 to 34, (R⁸)_(r) is defined as follows:

    ______________________________________                                                    (R.sup.8).sub.r                                                   ______________________________________                                                    3-Cl, 5-CF.sub.3                                                              3-Br, 5-CF.sub.3                                                              3-F, 5-CF.sub.3                                                               3, 5-(CF.sub.3).sub.2                                                         5-CF.sub.3                                                                    3, 5-Cl.sub.2                                                                 6-Cl                                                                          6-CF.sub.3                                                                    6-Br                                                              ______________________________________                                    

                  TABLE 35                                                        ______________________________________                                         ##STR74##                                                                    (R.sup.8).sub.r                                                                        R.sup.13                                                                              R.sup.14 R.sup.5                                                                           R.sup.6                                                                              p   R.sup.7                              ______________________________________                                        H        H       H        H   H      0   H                                    H        H       H        H   H      1   H                                    6-Cl     H       H        H   H      0   H                                    6-Cl     H       H        H   H      1   H                                    6-Br     H       H        H   H      0   H                                    6-Br     H       H        H   H      1   H                                    6-F      H       H        H   H      0   H                                    6-F      H       H        H   H      1   H                                    6-I      H       H        H   H      0   H                                    6-I      H       H        H   H      1   H                                    6-CH.sub.3                                                                             H       H        H   H      0   H                                    6-CH.sub.3                                                                             H       H        H   H      1   H                                    6-CF.sub.3                                                                             H       H        H   H      0   H                                    6-CF.sub.3                                                                             H       H        H   H      1   H                                    6-Cl     CH.sub.3                                                                              H        H   H      0   H                                    6-Cl     CH.sub.3                                                                              H        H   H      1   H                                    6-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    6-CH.sub.3                                                                             CH.sub. CH.sub.3 H   H      1   H                                    6-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    6-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    6-Cl     CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    6-Cl     CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    6-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    6-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    6-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    6-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    ______________________________________                                    

                  TABLE 36                                                        ______________________________________                                         ##STR75##                                                                    (R.sup.8).sub.r                                                                        R.sup.13                                                                              R.sup.14 R.sup.5                                                                           R.sup.6                                                                              p   R.sup.7                              ______________________________________                                        H        H       H        H   H      0   H                                    H        H       H        H   H      1   H                                    5-Cl     H       H        H   H      0   H                                    5-Cl     H       H        H   H      1   H                                    5-Br     H       H        H   H      0   H                                    5-Br     H       H        H   H      1   H                                    5-F      H       H        H   H      0   H                                    5-F      H       H        H   H      1   H                                    5-I      H       H        H   H      0   H                                    5-I      H       H        H   H      1   H                                    5-CH.sub.3                                                                             H       H        H   H      0   H                                    5-CH.sub.3                                                                             H       H        H   H      1   H                                    5-CF.sub.3                                                                             H       H        H   H      0   H                                    5-CF.sub.3                                                                             H       H        H   H      1   H                                    5-Cl     CH.sub.3                                                                              H        H   H      0   H                                    5-Cl     CH.sub.3                                                                              H        H   H      1   H                                    5-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    5-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    5-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    5-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    5-Cl     CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    5-Cl     CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    5-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    5-CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    5-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      0   H                                    5-CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3 H   H      1   H                                    ______________________________________                                    

                  TABLE 37                                                        ______________________________________                                         ##STR76##                                                                    (R.sup.8).sub.r                                                                      R.sup.11 R.sup.12                                                                             s      R.sup.5                                                                           R.sup.6                                                                             p   R.sup.7                           ______________________________________                                        H      H        H      1      H   H     1   H                                 H      H        H      2      H   H     1   H                                 5-Cl   H        H      1      H   H     1   H                                 5-Cl   H        H      2      H   H     1   H                                 5-CF.sub.3                                                                           H        H      1      H   H     1   H                                 5-CF.sub.3                                                                           H        H      2      H   H     1   H                                 ______________________________________                                    

                  TABLE 38                                                        ______________________________________                                         ##STR77##                                                                    (R.sup.8).sub.r                                                                        R.sup.13                                                                              R.sup.14 R.sup.5                                                                           R.sup.6                                                                              p   R.sup.7                              ______________________________________                                        H        H       H        H   H      1   H                                    H        H       H        H   H      2   H                                    6-Cl     H       H        H   H      1   H                                    6-Cl     H       H        H   H      2   H                                    6-Br     H       H        H   H      1   H                                    6-Br     H       H        H   H      2   H                                    6-F      H       H        H   H      1   H                                    6-F      H       H        H   H      2   H                                    6-I      H       H        H   H      1   H                                    6-I      H       H        H   H      2   H                                    6-CH.sub.3                                                                             H       H        H   H      1   H                                    6-CH.sub.3                                                                             H       H        H   H      2   H                                    6-CF.sub.3                                                                             H       H        H   H      1   H                                    6-CF.sub.3                                                                             H       H        H   H      2   H                                    ______________________________________                                    

                  TABLE 39                                                        ______________________________________                                         ##STR78##                                                                    (R.sup.8).sub.r                                                                        R.sup.13                                                                              R.sup.14 R.sup.5                                                                           R.sup.6                                                                              p   R.sup.7                              ______________________________________                                        H        H       H        H   H      1   H                                    H        H       H        H   H      2   H                                    5-Cl     H       H        H   H      1   H                                    5-Cl     H       H        H   H      2   H                                    5-Br     H       H        H   H      1   H                                    5-Br     H       H        H   H      2   H                                    5-F      H       H        H   H      1   H                                    5-F      H       H        H   H      2   H                                    5-I      H       H        H   H      1   H                                    5-I      H       H        H   H      2   H                                    5-CH.sub.3                                                                             H       H        H   H      1   H                                    5-CH.sub.3                                                                             H       H        H   H      2   H                                    5-CF.sub.3                                                                             H       H        H   H      1   H                                    5-CF.sub.3                                                                             H       H        H   H      2   H                                    ______________________________________                                    

                  TABLE 40                                                        ______________________________________                                         ##STR79##                                                                    (R.sup.8).sub.r                                                                     R.sup.11                                                                              R.sup.12                                                                              s    B     R.sup.5                                                                            R.sup.6                                                                            p    R.sup.7                       ______________________________________                                        H     H       H       1    COO   H    H    1    H                             H     H       H       2    COO   H    H    1    H                             H     H       H       1    COO   H    H    2    H                             H     H       H       2    COO   H    H    2    H                             6-CH.sub.3                                                                          H       H       1    COO   H    H    1    H                             6-CH.sub.3                                                                          H       H       2    COO   H    H    1    H                             6-CH.sub.3                                                                          H       H       1    COO   H    H    2    H                             6-CH.sub.3                                                                          H       H       2    COO   H    H    2    H                             ______________________________________                                    

                  TABLE 41                                                        ______________________________________                                         ##STR80##                                                                    Bonding                                                                       position of                                                                   heterocyclic                                                                  ring        B      (R.sub.8).sub.r                                                                        R.sup.5                                                                           R.sup.6                                                                             p   R.sup.7                             ______________________________________                                        2           COO    H        H   H     2   H                                   2           COO    H        H   H     3   H                                   3           COO    H        H   H     2   H                                   3           COO    H        H   H     3   H                                   2           O      H        H   H     1   H                                   2           O      H        H   H     2   H                                   2           O      H        H   H     3   H                                   2           S      H        H   H     1   H                                   2           S      H        H   H     2   H                                   2           S      H        H   H     3   H                                   2           NH     H        H   H     1   H                                   2           NH     H        H   H     2   H                                   2           NH     H        H   H     3   H                                   2           NH     H        H   H     1   H                                   2           NH     H        H   H     2   H                                   2           NH     H        H   H     3   H                                   ______________________________________                                    

                  TABLE 42                                                        ______________________________________                                         ##STR81##                                                                    (R.sup.8).sub.r                                                                          R.sup.5                                                                             R.sup.6      p   R.sup.7                                     ______________________________________                                        H          H     H            0   H                                           H          H     H            1   H                                           H          H     H            2   H                                           H          H     H            3   H                                           ______________________________________                                    

                  TABLE 43                                                        ______________________________________                                         ##STR82##                                                                    (R.sup.8).sub.r                                                                          R.sup.5                                                                             R.sup.6      p   R.sup.7                                     ______________________________________                                        3-Br, 5-CF.sub.3                                                                         H     H            1   H                                           3-Br, 5-CF.sub.3                                                                         H     H            2   H                                           3-Br, 5-CF.sub.3                                                                         H     H            3   H                                           3-Cl, 5-CF.sub.3                                                                         H     H            1   H                                           3-Cl, 5-CF.sub.3                                                                         H     H            2   H                                           3-Cl, 5-CF.sub.3                                                                         H     H            3   H                                           3-F, 5-CF.sub.3                                                                          H     H            1   H                                           3-F, 5-CF.sub.3                                                                          H     H            2   H                                           3-F, 5-CF.sub.3                                                                          H     H            3   H                                           3,5-(CF.sub.3).sub.2                                                                     H     H            1   H                                           3,5-(CF.sub.3).sub.2                                                                     H     H            2   H                                           3,5-(CF.sub.3).sub.2                                                                     H     H            3   H                                           5-CF.sub.3 H     H            1   H                                           5-CF.sub.3 H     H            2   H                                           5-CF.sub.3 H     H            3   H                                           ______________________________________                                    

                  TABLE 44                                                        ______________________________________                                         ##STR83##                                                                    (R.sup.8).sub.r                                                                             R.sup.5                                                                             R.sup.6     p   R.sup.7                                   ______________________________________                                        C.sub.6 H.sub.5                                                                             H     H           0   H                                         C.sub.6 H.sub.5                                                                             H     H           1   H                                         C.sub.6 H.sub.5                                                                             H     H           1   H                                         C.sub.6 H.sub.5                                                                             H     H           3   H                                         C.sub.6 H.sub.4 (4-Cl)                                                                      H     H           0   H                                         C.sub.6 H.sub.4 (4-Cl)                                                                      H     H           1   H                                         C.sub.6 H.sub.4 (4-Cl)                                                                      H     H           2   H                                         C.sub.6 H.sub.4 (4-Cl)                                                                      H     H           3   H                                         C.sub.6 H.sub.4 (4-CF.sub.3)                                                                H     H           0   H                                         C.sub.6 H.sub.4 (4-CF.sub.3)                                                                H     H           1   H                                         C.sub.6 H.sub.4 (4-CF.sub.3)                                                                H     H           2   H                                         C.sub.6 H.sub.4 (4-CF.sub.3)                                                                H     H           3   H                                         C.sub.6 H.sub.4 (4-OCF.sub.3)                                                               H     H           0   H                                         C.sub.6 H.sub.4 (4-OCF.sub.3)                                                               H     H           1   H                                         C.sub.6 H.sub.4 (4-OCF.sub.3)                                                               H     H           2   H                                         C.sub.6 H.sub.4 (4-OCF.sub.3)                                                               H     H           3   H                                         C.sub.6 H.sub.4 (4-Br)                                                                      H     H           0   H                                         C.sub.6 H.sub.4 (4-Br)                                                                      H     H           1   H                                         C.sub.6 H.sub.4 (4-Br)                                                                      H     H           2   H                                         C.sub.6 H.sub.4 (4-Br)                                                                      H     H           3   H                                         ______________________________________                                    

                  TABLE 45                                                        ______________________________________                                         ##STR84##                                                                    (R.sup.8).sub.r                                                                           R      B        R.sup.5                                                                           R.sup.6                                                                             p   R.sup.7                             ______________________________________                                        H           S      S        H   H     1   H                                   H           S      S        H   H     2   H                                   H           S      O        H   H     1   H                                   H           S      O        H   H     2   H                                   H           S      NH       H   H     1   H                                   H           S      NH       H   H     2   H                                   H           S      S        H   H     2   H                                   H           S      O        H   H     2   H                                   2-CF.sub.3  S      NH       H   H     2   H                                   2-CF.sub.3  S      S        H   H     2   H                                   2-CF.sub.3  S      O        H   H     2   H                                   3-CF.sub.3  S      NH       H   H     2   H                                   3-CF.sub.3  S      S        H   H     2   H                                   3-CF.sub.3  S      O        H   H     2   H                                   2-OCF.sub.3 S      NH       H   H     2   H                                   2-OCF.sub.3 S      S        H   H     2   H                                   2-OCF.sub.3 S      O        H   H     2   H                                   3-OCF.sub.3 S      NH       H   H     2   H                                   3-OCF.sub.3 S      S        H   H     2   H                                   3-OCF.sub.3 S      O        H   H     2   H                                   2-Cl        S      NH       H   H     2   H                                   2-Cl        S      S        H   H     2   H                                   2-Cl        S      O        H   H     2   H                                   3-Cl        S      NH       H   H     2   H                                   3-Cl        S      S        H   H     2   H                                   3-Cl        S      O        H   H     2   H                                   3-Cl        S      NH       H   H     2   H                                   2-Br        S      S        H   H     2   H                                   2-Br        S      O        H   H     2   H                                   2-Br        S      NH       H   H     2   H                                   3-Br        S      S        H   H     2   H                                   3-Br        S      O        H   H     2   H                                   3-Br        S      NH       H   H     2   H                                   3,4-(CH.sub.3).sub.2                                                                      S      S        H   H     2   H                                   3,4-(CH.sub.3).sub.2                                                                      S      O        H   H     2   H                                   3,4-(CH.sub.3).sub.2                                                                      S      NH       H   H     2   H                                   3-OCH.sub.3 S      S        H   H     2   H                                   3-OCH.sub.3 S      O        H   H     2   H                                   3-OCH.sub.3 S      NH       H   H     2   H                                   3-OCH.sub.2 CH.sub.3                                                                      S      S        H   H     2   H                                   3-OCH.sub.2 CH.sub.3                                                                      S      O        H   H     2   H                                   3-OCH.sub.2 CH.sub.3                                                                      S      NH       H   H     2   H                                   4-OCH.sub.3 S      S        H   H     2   H                                   4-OCH.sub.3 S      O        H   H     2   H                                   4-OCH.sub.3 S      NH       H   H     2   H                                   4-OCH.sub.2 CH.sub.3                                                                      S      S        H   H     2   H                                   4-OCH.sub.2 CH.sub.3                                                                      S      O        H   H     2   H                                   4-OCH.sub.2 CH.sub.3                                                                      S      NH       H   H     2   H                                   3-OCH(CH.sub.3).sub.2                                                                     S      S        H   H     2   H                                   3-OCH(CH.sub.3).sub.2                                                                     S      O        H   H     2   H                                   3-OCH(CH.sub.3).sub.2                                                                     S      NH       H   H     2   H                                   4-OCH(CH.sub.3).sub.2                                                                     S      S        H   H     2   H                                   4-OCH(CH.sub.3).sub.2                                                                     S      O        H   H     2   H                                   4-OCH(CH.sub.3).sub.2                                                                     S      NH       H   H     2   H                                   H           NH     S        H   H     1   H                                   H           NH     S        H   H     2   H                                   2-CH.sub.3  NH     S        H   H     1   H                                   2-CH.sub.3  NH     S        H   H     2   H                                   2-OCH.sub.3 NH     S        H   H     1   H                                   2-OCH.sub.3 NH     S        H   H     2   H                                   2-OCF.sub.3 NH     S        H   H     1   H                                   2-OCF.sub.3 NH     S        H   H     2   H                                   2-NO.sub.2  NH     S        H   H     1   H                                   2-NO.sub.2  NH     S        H   H     2   H                                   2-Cl        NH     S        H   H     1   H                                   2-Cl        NH     S        H   H     2   H                                   2-Br        NH     S        H   H     1   H                                   2-Br        NH     S        H   H     2   H                                   2-CH.sub.3  NH     O        H   H     1   H                                   2-CH.sub.3  NH     NH       H   H     2   H                                   2-OCH.sub.3 NH     O        H   H     1   H                                   2-OCH.sub.3 NH     NH       H   H     2   H                                   2-OCF.sub.3 NH     O        H   H     1   H                                   2-OCF.sub.3 NH     NH       H   H     2   H                                   2-Cl        NH     O        H   H     1   H                                   2-Cl        NH     NH       H   H     2   H                                   2-Br        NH     O        H   H     1   H                                   2-Br        NH     NH       H   H     2   H                                   H           O      S        H   H     1   H                                   H           O      O        H   H     1   H                                   H           O      NH       H   H     1   H                                   H           O      S        H   H     2   H                                   H           O      O        H   H     2   H                                   H           O      NH       H   H     2   H                                   2-Cl        O      S        H   H     2   H                                   2-Cl        O      O        H   H     2   H                                   2-Cl        O      NH       H   H     2   H                                   3-Cl        O      S        H   H     2   H                                   3-Cl        O      O        H   H     2   H                                   3-Cl        O      NH       H   H     2   H                                   2-CF.sub.3  O      S        H   H     2   H                                   2-CF.sub.3  O      O        H   H     2   H                                   2-CF.sub.3  O      NH       H   H     2   H                                   3-CF.sub.3  O      S        H   H     2   H                                   3-CF.sub.3  O      O        H   H     2   H                                   3-CF.sub.3  O      NH       H   H     2   H                                   2-OCF.sub.3 O      S        H   H     2   H                                   2-OCF.sub.3 O      O        H   H     2   H                                   2-OCF.sub.3 O      NH       H   H     2   H                                   3-OCF.sub.3 O      S        H   H     2   H                                   3-OCF.sub.3 O      O        H   H     2   H                                   3-OCF.sub.3 O      NH       H   H     2   H                                   2-NO.sub.2  NH     O        H   H     1   H                                   2-NO.sub.2  NH     NH       H   H     2   H                                   ______________________________________                                    

                  TABLE 46                                                        ______________________________________                                         ##STR85##                                                                    (R.sup.8).sub.r                                                                           R.sup.5                                                                             R.sup.6     p   R.sup.7                                     ______________________________________                                        H           H     H           1   H                                           H           H     H           2   H                                           ______________________________________                                    

The aldehyde compound of the general formula [VI], which is anintermediate for use in the production of the present compounds, can beproduced, for example, according to the following scheme 1: ##STR86##wherein all variables are as defined above.

The compounds of the general formula [II] or [III], which areintermediate for use in the production of the present compounds, can beproduced, for example, according to the following schemes 2 to 6:##STR87##

The compounds of the general formula [VII], which are intermediates foruse in the production of the present compounds, can be produced, forexample, according to the following scheme 7: ##STR88##

The compounds of the general formula [IV] and the alcohol compounds ofthe general formula [V], which are intermediates for use in theproduction of the present compounds, can be produced, for example,according to the following scheme 8: ##STR89## wherein L² is chlorine orbromine, L³ is mesyloxy or tosyloxy, and X is as defined above.

The compounds of the general formula [VIII] or [IX] wherein R¹ is R¹ ₁(wherein R¹ ₁ is Q₁ or Q₂ in the definition of R¹), which areintermediates for use in the production of the present compounds, can beobtained from various commercial sources or can be produced, forexample, according to the schemes 9 and 10 depicted below.

The aldehyde compounds of the general formula: A--CHO (wherein A is asdefined above), which are the starting compounds in the production ofthe compounds [VIII] or [IX], can be obtained, for example, by theprocesses disclosed in the following references.

Furancarbaldehydes:

Zh. Org. Khim., 11, 1955;

Tetrahedron., 39, 3881;

Chem. Pharm. Bull., 28, 2846

Thiophenecarbaldehydes:

Tetrahedron., 32, 1403;

J. Org. Chem., 41, 2835;

Zh. Obshch. Khim., 34, 4010;

Bull. Soc. Chim. France., 479 (1963)

Pyrrolecarbaldehydes:

Beilstein., 21, 1279

Isothiazolecarbaldehydes:

J. Medicin. Chem., 13, 1208;

J. Chem. Soc., 446 (1964)

Pyrazolecarboaldehydes:

Chem. Ber., 97, 3407;

J. Chem. Soc., 3314 (1957)

Imidazolecarbaldehydes:

J. Pharm. Soc. Japan., 60, 184;

J. Amer. Chem. Soc., 71, 2444

Thiazolecarbaldehydes:

JP-A 59-206370/1984

Chem. Ab., 62, 7764d;

Chem. Ber., 101, 3872;

JP-A 59-206370/1984

Thiadiazolecarbaldehydes:

U.S. Pat. No. 1,113,705 ##STR90## wherein all the variables are each asdefined above. ##STR91## wherein all the variables are each as definedabove.

The compounds of the general formula: A-L' (wherein L' is halogen (e.g.,chlorine, bromine, iodine)) included in the compounds [XI], which areintermediates for use in the production of the present compounds, can beobtained from various commercial sources or can be produced, forexample, according to the following scheme 11: ##STR92## wherein A andL' are each as defined above.

The compounds [X], [XII] or [XIII], which are intermediates for use inthe production of the present compounds, can be produced, for example,according to the following schemes 12 and 13: ##STR93## wherein all thevariables are each as defined above.

*) J. Amer. Chem. Soc., 33, 440 (1905) ##STR94## wherein M_(s) is mesyl;T_(s) is tosyl; R¹⁶ is a protecting group for alcohols (e.g., benzoyl);R¹⁷ is protected formyl (e.g., acetal); L¹ is hydroxy or L; and R², R³,R⁷, R¹⁰, R¹¹, R¹⁴, X, L, p and t are each as defined above. ##STR95##wherein all the variables are each as defined above.

The present compounds are satisfactorily effective for the control ofvarious noxious insects, mites and ticks, examples of which are asfollows:

Hemiptera:

Delphacidae such as Laodelphax striatellus, Nilaparvata lugens andSogatella furcifera, Deltoceplialidae such as Nephotettix cincticeps andNephotettix virescens, Aphididae, Pentatomidae, Aleyrodidae, Coccidae,Tinigidae, Psyllidae, etc.

Lepidoptera:

Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinianubilalis, Parapediasia teterrella, Notarcha derogata and Plodiainterpunctella, Noctuidae such as Spodoptera litura, Spodoptera exigua,Spodoptera littoralis, Pseudaletia separata, Mamestra brassicae, Agrotisipsilon, Trichoplusia spp., Heliothisspp., Helicoverpa spp. and Eariasspp., Pieridae such as Pieris rapae crucivora, Tortricidae such asAdoxophyes spp., Grapholita molesta and Cydia pomonella, Carposinidaesuch as Carposina niponensis, Lyonetiidae such as Lyonetia spp.,Lymantriidae such as Lymantria spp. and Euproctis spp., Yponomeutidaesuch as Plutella xylostella, Gelechiidae such as Pectinophorngossypiella, Arctiidae such as Hyphantria cunea, Tineidae such as Tineatranslucens and Tineola bisselliella, etc.

Diptera:

Culex such as Culex pipiens pallens and Cules tritaeniorhynchus, Aedessuch as Aedes albopictus and Aedes aegypti, Anopheles such asAnophelinae sinensis, Chironomidae, Muscidae such as Musca domestica andMuscina stabulans, Calliphoridae, Sarcophagidae, Fannia canicularis,Anthomyiidae such as Delia Platura and Delia antigua, Trypetidae,Drosophilidae, Psychodidae, Tabanidae, Simuliidae, Stomoxyinae, etc.

Coleoptera:

Diabrotica such as Diabrotica virgifera and Diabrotica undecimpunctata,Scarabaeidae such as Anomala cuprea and Anomala rufocuprea,Curculionidae such as Lissorphoptrus oryzophilus, Hypera pastica, andCalosobruchys chinensis, Tenebrionidae such as Tenebrio molitor andTribolium castaneum, Chrysomelidae such as Phyllotreta striolata andAulacophora femoralis, Anobiidae, Epilachna spp. such as Henosepilachnavigintioctopunctata, Lyctidae, Bostrychidae, Cerambycidae, Paederusfiuscipes, etc.

Dictyoptera:

Blattella germanica, Periplaneta fuliginosa, Peroplaneta americana,Periplaneta brunnea, Blatta orientalis, etc.

Thysanoptera:

Thrips palmi, Thrips hawaiiensis, etc.

Hymenoptera:

Formicidae, Vespidae, Bethylidae, Tenthredinidae such as Athalia rosaejaponensis, etc.

Orthoptera:

Gryllotalpidae, Acrididae, etc.

Siphonaptera:

Purex irritans, etc.

Anoplura:

Pediculus hurmanus capitis, Phthirus pubis, etc.

Isoptera (termites):

Reticulitermes speratus, Coptotermes formosanus, etc.

Acarina:

plant patasitic Tetranychidae such as Tetranychus uriticae, Panonychuscitri, Tetranychus cinnabarinus and Panonychus ulmi, animal parasiticIxodidae such as Boophilus microphus, house dust mites, etc.

The present compounds are also effective for the control of variousnoxious insects, mites and ticks having resistance to conventionalinsecticides and acaricides.

When the present compound is used as an active ingredient ofinsecticidal/acaricidal agents, it may be used as such without anyaddition of other ingredients. The present compound is, however, usuallyformulated into a dosage form such as oil sprays, emulsifiableconcentrates, wettable powders, flowables, granules, dusts, aerosols,fumigants (foggings) and poison baits. These formulations are usuallyprepared by mixing the present compound with a solid carrier, a liquidcarrier, a gaseous carrier or a bait, and if necessary, adding asurfactant and other auxiliaries used for formulation.

Each of the formulations usually contains the present compound as anactive ingredient in an amount of 0.01% to 95% by weight.

Examples of the solid carrier to be used for the formulation are finepowder or granules of clay materials such as kaolin clay, diatomaceousearth, synthetic hydrated silicon oxide, bentonite, Fubasami clay andacid clay; various kinds of talc, ceramics, other inorganic mineralssuch as sericite, quartz, sulfur, active carbon, calcium carbonate andhydrated silica; and chemical fertilizers such as ammonium sulfate,ammonium phosphate, ammonium nitrate, urea and ammonium chloride.

Examples of the liquid carrier are water; alcohols such as methanol andethanol; ketones such as acetone and methyl ethyl ketone; aromatichydrocarbons such as benzene, toluene, xylene, ethylbenzene andmethylnaphthalene; aliphatic hydrocarbons such as hexane, cyclohexane,kerosine and gas oil; esters such as ethyl acetate and butyl acetate;nitriles such as acetonitrile and isobutyronitrile; ethers such asdiisopropyl ether and dioxane; acid amides such as N,N-dimethylformamideand N,N-dimethylacetamide; halogenated hydrocarbons such asdichloromethane, trichloroethane and carbon tetrachloride; dimethylsulfoxide; and vegetable oils such as soybean oil and cottonseed oil.

Examples of the gaseous carrier or propellant are flon gas, butane gas,LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.

Examples of the surfactant are alkyl sulfates, alkyl sulfonates, alkylarylsulfonates, alkyl aryl ethers and their polyoxyethylene derivatives,polyethylene glycol ethers, polyhydric alcohol esters and sugar alcoholderivatives.

Examples of the auxiliaries used for formulation, such as fixing agentsor dispersing agents, are casein, gelatin, polysaccharides such asstarch, gum arabic, cellulose derivatives and alginic acid, ligninderivatives, bentonite, sugars, and synthetic water-soluble polymerssuch as polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid.

Examples of the stabilizer are PAP (isopropyl acid phosphate), BHT(2,6-di-tert-butyl-4-methylphenol), BHA (mixtures of2-t-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetableoils, mineral oils, surfactants, fatty acids and their esters.

Examples of the base material to be used in the poison baits are baitmaterials such as grain powder, vegetable oils, sugars and crystallinecellulose; antioxidants such as dibutylhydroxytoluene andnordihydroguaiaretic acid; preservatives such as dehydroacetic acid;substances for preventing erroneous eating, such as red pepper powder,attractant flavors such as cheese flavor or onion flavor.

The formulation thus obtained is used as such or after diluted withwater. The formulation may also be used in combination with otherinsecticides, nematocides, acaricides, bactericides, fungicides,herbicides, plant growth regulators, synergists, fertilizers, soilconditioners and/or animal feed under non-mixing conditions or premixingconditions.

Examples of the insecticide, acaricide and/or nematocide which can beused are organophosphorus compounds such as Fenitrothion [(O,O-dimethylO-(3-methyl-4-nitrophenyl)phosphorothioate], Fenthion [O,O-dimethylO-(3-methyl-4-methylthio)phenyl)phophorothioate], Diazinon[O,O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-ylphosphorothioate],Chlorpyriphos [O,O-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate],Acephate [O,S-dimethylacetylphosphoramidothioate], Methidachion[S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethylO,O-dimethylphosphorodithioate], Disulfoton [O,O-diethylS-2-ethylthioethylphosphorothioate], DDVP[2,2-dichlorovinyldimethylphosphate], Sulprofos [O-ethylO-4-(methylthio)phenyl S-propyl phosphorodithioate], Cyanophos[O-4-cyanophenyl O,O-dimethylphosphorothioate], Dioxabenzofos[2-methoxy-4H-1,3,2-benzodioxaphosphinin-2-sulfide], Dimethoate[O,O-dimethyl--S--(N-methylcarbamoylmethyl)dithiophosphate], Phenthoate[ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], Malathion[diethyl(dimethoxyphosphinothioylthio)succinate], Trichlorfon [dimethyl2,2,2-trichloro-1-hydroxyethylphosphonate], Azinphos-methyl[S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl-O,O-dimethylphosphorodithioate],Monocrotophos [dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinylphosphate],Ethion [O,O,O',O'-tetraethyl S,S'-methylenebis(phosphorodithioate)] andProfenfos [O-4-bromo-2-chlorophenyl O-ethyl S-propylphosphorothioate];carbamate compounds such as BPMC [2-secbutylphenylmethylcarbamate],Benfuracarb [ethylN-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β-alaninate],Propoxur [2-isopropoxyphenyl N-methylcarbamate], Carbosulfan[2,3-dihydro-2,2-dimethyl-7-benzo[b]furanylN-dibutylaminothio-N-methylcarbamate], Carbaril[1-naphthyl-N-methylcarbamate], Methomyl[S-methyl-N-[(methylcarbamoyl)oxy]thioacetoimidate], Ethiofencarb[2-(ethylthiomethyl)phenylmethylcarbamate], Aldicarb[2-methyl-2-(methylthio)propanaldehyde O-methylcarbamoyloxime], Oxamyl[N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide],Alanylcarb [ethyl(Z)-N-benzyl-N-{[methyl(1-methylthioethylideneaminooxycarbonyl)amino]thio}-β-alanylate],Fenothiocarb [S-(4-phenoxybutyl)-N,N-dimethylthiocarbamate] andThiodicarb[3,7,9,13-tetramethyl-5,11-dioxa2,8,14-trithia-4,7,9,12-tetraazapentadeca-3,12-dien-6,10-dione];pyrethroid compounds such as Etofenprox[2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzylether], Fenvalerate[(RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate],Esfenvalerate [(S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrin[(RS)-α-cyano-3-phenoxybenzyl2,2,3,3-tetramethylcyclopropanecarboxylate], Cypermethrin[(RS)-α-cyano-3-phenoxybenzyl(1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate],Permethrin [3-phenoxybenzyl(1RS,3RS)-3-(2,2dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate],Cyhalothrin [(RS)-α-cyano-3-phenoxybenzyl(Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate],Deltamethrin [(S)-α-cyano-m-phenoxybenzyl(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate],Cycloprothrin [(RS)-α-cyano-3-phenoxybenzyl(RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate],Fluvalinate [α-cyano-3-phenoxybenzylN-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinate], Bifenthrin[2-methylbiphenyl-3-ylmethyl)(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoropropen-1-yl)-2,2-dimethylcyclopropanecarboxylate],Acrinathrin [cyano-(3-phenoxyphenyl)methyl[1R-{1α(S*),3α(Z)}]-2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy-1-propenyl]cyclopropanecarboxylate],2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl (3-phenoxybenzyl) ether,Traromethrin [(S)-α-cyano-3-phenoxylbenzyl (1R,3R)-3-[(1'RS)(1,1',2',2'-tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylate]and Silafluofen [4-ethoxylphenyl[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane]; thiadiazinederivatives such as Buprofezin[2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5thiadiazin-4-one];nitroimidazolidine derivatives such as Imidacloprid[1-(6-chloro-3pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine];Nereistoxin derivatives such as Cartap[S,S'-(2-dimethylaminotrimethylene)bisthiocarbamate], Thiocyclam[N,N-dimethyl-1,2,3-trithian-5-ylamine] and Bensultap[S,S'-2-dimethylaminotrimethylene di(benzenethiosulfonate)];N-cyanoamidine derivatives such as acetamiprid[N-cyano-N'methyl-N'-(6-chloro-3-pyridylmethyl)acetamidine]; chlorinatedhydrocarbons such as Endosulfan[6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3benzodioxathiepinoxide],γ-BHC [1,2,3,4,5,6-hexachlorocyclohexane] and Kelthane[1,1-bis(chlorophenyl)-2,2,2-trichloroethanol]; benzoylphenylureacompounds such as Chlorfluazuron[1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3(2,6-difluorobenzoyl)urea],Teflubenzuron[1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6difluorobenzoyl)urea] andFulphenoxron[1-(4-(2-chloro-4-trifluoromethylphenoxy)-2fluorophenyl)-3-(2,6-difluorobenzoyl)urea];formamidine derivatives such as Arnitraz[N,N'-[(methylimino)dimethylidine]-di-2,4-xylidine] and Chlordimeform[N'-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide]; thioureaderivatives such as Diafenthiuron[N-(2,6-diisopropyl-4-phenoxyphenyl)-N'-tert-butylcarbodiimide];Fipronyl [5-amino-1-(2,6-dichloro-α,60,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3carbonitrite],Tebfenozide[N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide],4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile, Chlorfenapyl[4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-S-trifluoromethylpyrole-3-carbonitril],Bromopropylate [isopropyl 4,4'-dibromobenzylate], Tetradifon[4-chlorophenyl-2,4,5-trichlorophenyl sulfone], Quinomethionate[S,S-6-methylquinoxaline-2,3-diyldithiocarbonate], Propargite[2-(4-tert-butylphenoxy)cyclohexyl prop-2-yl sulfite], Fenbutatin oxide[bis[tris(2-methyl-2-phenylpropyl)tin)oxide], Hexythiazox [(4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], Chlofentezine[3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine], Pyridaben[2-tertbutyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H) one],Fenpyroximate[tert-butyl(E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoate],Tebfenpyrad[N-4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolcarboxamide],polynactin complexes including tetranactin, dinactin and trinactin;Milbemectin, Avermectin, Ivermectin, Azadilactin [AZAD], Pyrimidifen[5-chloro-N-[2-{4-(2-ethoxyethyl)2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine]and Pimetrozine[2,3,4,5-tetrahydro-3-oxo-4-[(pyridin-3-yl)-methyleneamino]-6-methyl-1,2,4-triazine].

When the present compound is used as an active ingredient ofinsecticidal/-acaricidal agents for agriculture, the application amountthereof is usually in the range of 0.1 to 100 g per 10 ares. In the caseof emulsifiable concentrates, wettable powders and flowableconcentrates, which are used after diluted with water, the applicationconcentration thereof is usually in the range of 0.1 to 500 ppm. In thecase of granules and dusts, they are applied as such without anydilution. When the present compound is used as an active ingredient ofinsecticidal/acaricidal agents for epidemic prevention, it is formulatedinto a dosage form such as emulsifiable concentrates, wettable powdersand flowable concentrates, which are applied after diluted with water toa typical concentration of 0.1 to 500 ppm; or it is formulated into adosage form such as oil sprays, aerosols, fumigants and poisonous baits,which are applied as such without any dilution.

The application amount and application concentration may vary dependingupon various conditions such as formulation type, application time,place and method, kind of noxious insects, mites and ticks, and degreeof damage, and they can be increased or decreased without limitation tothe above range.

The present invention will be further illustrated by the followingproduction examples, formulation examples and test examples, which arenot to be construed to limit the scope thereof.

The following are production examples for the present compoundsaccording to various production processes.

PRODUCTION EXAMPLE 1:

Production of compound (10) by production process E

To a solution of 0.44 g of4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.20 g of2-(2-hydroxyethyl)thiophene and 0.40 g of triphenylphosphine dissolvedin 10 ml of tetrahydrofuran was added dropwise a solution of 0.31 g ofdiisopropyl azodicarboxylate dissolved in 5 ml of tetrahydrofuran, whilestirring at room temperature. After stirring at room temperature for 12hours, the reaction mixture was concentrated, to which 20 ml of diethylether was added, and the precipitate was filtered. The filtrate wasconcentrated, and the residue was subjected to silica gelchromatography, which afforded 0.38 g of3,5-dichloro-4-(2-(2-thienyl)ethoxy)-1-(3,3-dichloro-2propenyloxy)benzene(62% yield), n_(D) ²⁵.6 1.5919.

PRODUCTION EXAMPLE 2:

Production of compound (1) by production process D

To a mixture of 0.40 g of2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.21 g of potassiumcarbonate and 20 ml of N,N-dimethylformamide was added dropwise asolution of 0.25 g of 6-chloro-3-(chloromethyl)pyridine dissolved in 5ml of N,N-dimethylformamide, while stirring at room temperature. Afterstirring at room temperature for 7 hours, the reaction mixture waspoured into ice-water, and extracted twice with 50 ml of diethyl ether.The combined ether layer was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduct was subjected to silica gel chromatography, which afforded 0.44g of 3,5-dichloro-4-(6-chloro-3-pyridylmethyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (77% yield), m.p. 93.3° C.

PRODUCTION EXAMPLE 3:

Production of compound (9) by production process E

To a solution of 0.43 g of4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.16 g of4-(hydroxymethyl)pyridine and 0.39 g of triphenylphosphine dissolved in10 ml of tetrahydrofuran was added dropwise a solution of 0.30 g ofdiisopropyl azodicarboxylate dissolved in 5 ml of tetrahydrofuran, whilestirring at room temperature. After stirring at room temperature for 12hours, the reaction mixture was concentrated, to which 20 ml of diethylether was added, and the precipitate was filtered. The filtrate wasconcentrated, and the residue was subjected to silica gelchromatography, which afforded 0.29 g of3,5-dichloro-4-(4-pyridylmethyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(51% yield), m.p. 74.0° C.

PRODUCTION EXAMPLE 4:

Production of compound (25) by production process H

A reaction vessel was charged with 0.20 g of3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene,0.08 g of thiophene-2-carboxylic acid, 0.08 g of potassium carbonate and10 ml of N,N-dimethylformamide. After stirring at room temperature for12 hours, the reaction mixture was poured into water, and extractedtwice with 30 ml of diethyl ether. The combined ether layer was washedwith water, dried with anhydrous magnesium sulfate, and concentrated toobtain a crude product. The crude product was subjected to silica gelchromatography, which afforded 0.18 g of3,5-dichloro-4-(3-(thiophene-2-carboxylate)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(81% yield), n_(D) ²⁴.0 1.5814.

PRODUCTION EXAMPLE 5:

Production of compound (29) by production process E

To a mixture of 0.4 g of2-[2-(4-chlorophenyl)-1,3-dioxolan-4-yl]ethanol, 0.46 g oftriphenylphosphine and 6 ml of tetrahydrofuran was added dropwise 0.35ml of diisopropyl azodicarboxylate, while stirring at room temperature.After further stirring for 15 minutes, a solution of 0.5 g of4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol in 2 ml oftetrahydrofuran was added. After stirring continued at room temperaturefor 3 hours, the reaction mixture was concentrated, and the residue wassubjected to silica gel chromatography, which afforded 0.3 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)4-[2-[2-(4-chlorophenyl)-1,3-dioxolan-4yl]ethoxy]benzene(35% yield), m.p. 84.1° C.

PRODUCTION EXAMPLE 6:

Production of compound (45) by production process E

To a solution of 0.33 g of2-(3-hydroxypropyloxy)-5-trifluoromethylpyridine, 0.40 g of2-chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol and 0.41 g oftriphenylphosphine dissolved in 30 ml of dichloromethane was addeddropwise a solution of 0.32 g of diisopropyl azodicarboxylate dissolvedin 3 ml of dichloromethane, while stirring at room temperature. Afterstirring at room temperature for 24 hours, the reaction mixture wasconcentrated to obtain a residue. The residue was subjected to silicagel chromatography, which afforded 0.56 g of3-chloro-5-methyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene(92% yield), n_(D) ²³.6 1.5294.

PRODUCTION EXAMPLE 7:

Production of compound (46) by production process E

To a solution of 0.26 g of2-(4-hydroxybutyloxy)-5-trifluoromethylpyridine, 0.3 g of2-chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol and 0.31 g oftriphenylphosphine dissolved in 30 ml of dichloromethane was addeddropwise a solution of 0.24 g of diisopropyl azodicarboxylate dissolvedin 5 ml of dichloromethane, while stirring at room temperature. Afterstirring at room temperature for 24 hours, the reaction mixture wasconcentrated to obtain a residue. The residue was subjected to silicagel chromatography, which afforded 0.50 g of3-chloro-5-methyl4-[4-(5-trifluoromethyl-2-pyridyloxy)butyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene(89% yield), n_(D) ²³.0 1.5275.

PRODUCTION EXAMPLE 8:

Production of compound (47) by production process A

In 10 ml of N,N-dimethylformamide were dissolved 0.7 g of3-ethyl-5methyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]phenoland 0.27 g of potassium carbonate, to which a solution of 0.34 g of1,1,3-trichloropropene dissolved in 5 ml of N,N-dimethylformamide wasadded dropwise, while stirring at room temperature. After stirring atroom temperature for 12 hours, the reaction mixture was poured intoice-water, and extracted twice with 100 ml of diethyl ether. Thecombined diethyl ether was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduce was subjected to silica gel chromatography, which afforded 0.6 gof3-ethyl-5-methyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene(65% yield), n_(D) ²³.0 1.5188.

PRODUCTION EXAMPLE 9:

Production of compound (48) by production process A

In 10 ml of N,N-dimethylformamide were dissolved 0.6 g of3-ethyl-5methyl-4-[4-(5-trifluoromethyl-2-pyridyloxy)butyloxy]phenol and0.23 g of potassium carbonate, to which a solution of 0.28 g of1,1,3-trichloropropene dissolved in 5 ml of N,N-dimethylformamide wasadded dropwise, while stirring at room temperature. After stirring atroom temperature for 12 hours, the reaction mixture was poured intoice-water, and extracted twice with 100 ml of diethyl ether. Thecombined diethyl ether was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduce was subjected to silica gel chromatography, which afforded 0.50g of3-ethyl-5-methyl-4-[4-(5-trifluoromethyl-2-pyridyloxy)butyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene(64% yield), n_(D) ²³.0 1.5170.

PRODUCTION EXAMPLE 10:

Production of compound (50) by production process A

In 10 ml of N,N-dimethylformamide were dissolved 0.45 g of3,5-diethyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]phenol and0.17 g of potassium carbonate, to which a solution of 0.18 g of1,1,3-trichloropropene dissolved in 5 ml of N,N-dimethylformamide wasadded dropwise, while stirring at room temperature. After stirring atroom temperature for 12 hours, the reaction mixture was poured intoice-water, and extracted twice with 100 ml of diethyl ether. Thecombined diethyl ether was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduce was subjected to silica gel chromatography, which afforded 0.35g of3,5-diethyl-4-[3-(5-trifluoromethyl-2-pyridyloxy)propyloxy]-1-(3,3-dichloro-2-propenyloxy)benzene(60% yield), n_(D) ²⁰.0 1.5192.

PRODUCTION EXAMPLE 11:

Production of compound (49) by production process H

A mixture of 1.0 g of1-(3-bromopropyloxy)-2,6-dichloro-4-(3,3-dichloro-2propenyloxy)benzeneand 4.0 g of 2-amino-5-(trifluoromethyl)pyridine was stirred at 90° C.for 3 hours. The reaction mixture was cooled to room temperature, andsubjected to silica gel chromatography, which afforded 0.14 g of3,5-dichloro-1-(3,3-dichloro-2propenyloxy)-4-(3-(5-(trifluoromethyl)-2-pyridylamino)propyloxy)benzene(12% yield), n_(D) ²⁵.0 1.5525.

Production Example 12:

Production of compound (36) by production process A

A mixture of 0.5 g of3,5-dichloro-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propyloxy]phenol,0.25 g of 1,1,3-trichloropropene, 0.2 g of potassium carbonate and 3 mlof N,N-dimethylformamide was stirred at room temperature overnight. Thereaction mixture was subjected to silica gel chromatography, whichafforded 0.3 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)propyloxy]benzene(47% yield), n_(D) ²⁰.5 1.5377.

PRODUCTION EXAMPLE 13:

Production of compound (36) by production process F

First, 2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine wasprepared as follows.

A mixture of 12.6 g of 1,3-propanediol and 100 ml ofN,N-dimethylformamide was stirred under a nitrogen stream, to which 3.30g of an oily mixture containing 60% sodium hydride was added in smallportions at room temperature over 30 minutes. After further stirringcontinued at room temperature for 1 hour, 20 ml of a DMF solution of10.0 g of 2-chloro-5-trifluoromethylpyridine was added dropwise over 40minutes. After further stirring continued under a nitrogen stream atroom temperature overnight, 100 ml of about 2 N diluted hydrochloricacid was added over 15 minutes to stop the reaction. The reactionmixture was extracted twice with toluene at a total volume of 500 ml.The combined toluene layer was successively washed with dilutedhydrochloric acid and aqueous sodium bicarbonate solution, dried withmagnesium sulfate, and concentrated to obtain an oily product. The oilyproduct was dissolved in 300 ml of hexane by heating, followed byrecrystallization, which afforded 5.3 g of2-(3-hydroxypropyloxy)-5-trifluoromethylpyridine as almost pure crystals(44% yield), m.p. 46.6° C.

A mixture of 4.0 g of 2-(3-hydroxypropyloxy)-5-trifluoromethylpyridine,3.4 ml of triethylamine and 25 ml of toluene was vigorously stirredunder a nitrogen stream, while cooling in chilled water bath to 5° C.Then, 1.63 g of methanesulfonyl chloride was added dropwise to thismixture at such a rate that the reaction temperature did not exceed 10°C., and the chilled water bath was removed. After further stirringcontinued at room temperature for 1.5 hours, 250 ml of water was addedthereto, and the mixture was vigorously stirred for further 30 minutes,followed by phase separation. The toluene layer was washed once withwater, dried with magnesium sulfate, and concentrated, which afforded 5g of 2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine as anoily product (92% yield).

¹ H-NMR δ(ppm) [CDCl₃, TMS] 8.39 (1H, br, s), 7.75 (1H, dd), 6.80 (1H,d), 4.0-5.0 (4H), 3.00 (3H, s), 2.30 (2H, quint.)

A mixture of 5 g of2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine, 5 g of4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 2.64 g of potassiumcarbonate and 300 ml of N,N-dimethylformamide was vigorously stirred atroom temperature for 4 days. Then, 300 ml of 2 N hydrochloric acid wasadded to this mixture, and extracted twice with toluene at a totalvolume of 300 ml. The combined toluene layer was successively washedwith 2 N hydrochloric acid and aqueous sodium bicarbonate solution,dried with magnesium sulfate, and concentrated to obtain about 8 g of anoily product. The oily product was subjected to silica gelchromatography, which afforded 6.0 g of3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)propyloxy]benzene(70% yield).

The following are specific examples of the present compound under thecorresponding compound numbers with their physical properties, ifmeasured.

    ______________________________________                                        (1)  3,5-Dichloro-4-(6-chloro-3-pyridylmethyloxy)-                                                          m.p. 93.3° C.                                 1-(3,3-dichloro-2-propenyloxy)benzene                                    (2)  3,5-Dichloro-4-(2,6-dichloro-3-pyridyl-                                                                m.p. 73.3° C.                                 methyloxy)-1-(3,3-dichloro-2-propenyl-                                        oxy)benzene                                                              (3)  3,5-Dichloro-4-(2-(1-pyrazolynyl)ethoxy)-                                                              m.p. 59.8° C.                                 1-(3,3-dichloro-2-propenyloxy)benzene                                    (4)  3,5-Dichloro-4-(2-(1-pyrazolynyl(ethoxy)-1-(3,3-                                                       m.p. 55.3° C.                                 dibromo-2-propenyloxy)benzene                                            (5)  3,5-Dichloro-4-(2-pyridylmethyloxy)-1-(3,3-                                                            m.p. 48.2° C.                                 dichloro-2-propenyloxy)benzene                                           (6)  3,5-Dichloro-4-(2-thienylmethyloxy)-1-(3,3-                                                            m.p. 44.6° C.                                 dichloro-2-propenyloxy)benzene                                           (7)  3,5-Dichloro-4-(2-furanylmethyloxy)-1-(3,3-                                                            m.p. 46.0° C.                                 dichloro-2-propenyloxy)benzene                                           (8)  3,5-Dichloro-4-(3-pyridylmethyloxy)-1-(3,3-                                                            m.p. 105.9° C.                                dichloro-2-propenyloxy)benzene                                           (9)  3,5-Dichloro-4-(4-pyridylmethyloxy)-1-(3,3-                                                            m.p. 74.0° C.                                 dichloro-2-propenyloxy)benzene                                           (10) 3,5-Dichloro-4-(2-(2-thienyl)ethoxy)-1-(3,3-                                                           n.sub.D.sup.25.6 1.5919                              dichloro-2-propenyloxy)benzene                                           (11) 3,5-Dichloro-4-(2-(3-methylthiazol-2-yl)ethoxy)-                                                       m.p. 30.4° C.                                 1-(3,3-dichloro-2-propenyloxy)benzene                                    (12) 3,5-Dichloro-4-(2,4,5-trichloroimidazolynyl-                                                           m.p. 67.5° C.                                 methyloxy)-1-(3,3-dichloro-2-                                                 propenyloxy)benzene                                                      (13) 3,5-Dichloro-4-(3,5-dimethyl-4-isoxazolynyl-                                                           m.p. 127.4° C.                                methyloxy)-1-(3,3-dichloro-2-                                                 propenyloxy)benzene                                                      (14) 3,5-Dichloro-4-(2-(3-thienyl)ethoxy)-1-(3,3-                                                           n.sub.D.sup.24.0 1.5916                              dichloro-2-propenyloxy)benzene                                           (15) 3,5-Dichloro-4-(3-(4-pyridyl)propyloxy)-1-(3,3-                                                        n.sub.D.sup.24.1 1.5566                              dichloro-2-propenyloxy)benzene                                           (16) 3,5-Dichloro-4-((2-(1,4-benzodi-                                                                       n.sub.D.sup.24.6 1.5799                              oxanyl))methoxy)-1-(3,3-dichloro-2-                                           propenyloxy)benzene                                                      (17) 3,5-Dichloro-4-((2-(5-formyl)furanyl)methoxy)-                                                         m.p. 91.5° C.                                 1-(3,3-dichloro-2-propenyloxy)benzene                                    (18) 3,5-Dichloro-4-((3-(6-methylpyridyl))methoxy)-                                                         m.p. 86.7° C.                                 1-(3,3-dichloro-2-propenyloxy)benzene                                    (19) 3,5-Dichloro-4-(2-(4-pyridylthio)ethoxy)-1-(3,3-                                                       m.p. 74.7° C.                                 dichloro-2-propenyloxy)benzene                                           (20) 3,5-Dichloro-4-(3-(3-pyridyl)propyloxy)-1-(3,3-                                                        m.p. 48.3° C.                                 dichloro-2-propenyloxy)benzene                                           (21) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.22.5 1.5674                              propenyloxy)phenoxy)propyl nicotinate                                    (22) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.22.5 1.5667                              propenyloxy)phenoxy)propyl isonicotinate                                 (23) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.25.5 1.6002                              propenyloxy)phenoxy)propyl quinolinate                                   (24) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.24.0 1.5589                              propenyloxy)phenoxy)propyl 2-furanate                                    (25) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.24.0 1.5814                              propenyloxy)phenoxy)propyl 2-thiophenate                                 (26) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.24.0 1.5788                              propenyloxy)phenoxy)propyl 3-thiophenate                                 (27) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     n.sub.D.sup.24.0 1.5737                              propenyloxy)phenoxy)propyl picolinate                                    (28) 3-(2,6-Dichloro-4-(3,3-dichloro-2-                                                                     m.p. 92.3° C.                                 propenyloxy)phenoxy)propyl 3-quinolinate                                 (29) 3,5-Dichloro-4-(2-(2-((2-(4-chlorophenyl)-1,3-                                                         m.p. 84.1° C.                                 dioxanyl)))ethoxy)-1-(3,3-dichloro-2-                                         propenyloxy)benzene                                                      (30) 3,5-Dichloro-4-(3-(2-pyridylthio)propyloxy)-1-                                                         n.sub.D.sup.22.5 1.5982                              (3,3-dichloro-2-propenyloxy)benzene                                      (31) 3,5-Dichloro-4-(2-(6-ethoxy-2-                                                                         m.p. 80.6° C.                                 benzothiezolyl)ethoxy)-1-(3,3-dichloro-2-                                     propenyloxy)benzene                                                      (32) 3,5-Dichloro-4-(2-(2-benzoxazolyl)ethoxy)-1-                                                           m.p. 61.2° C.                                 (3,3-dichloro-2-propenyloxy)benzene                                      (33) 3,5-Dichloro-4-(2-methyl-2-(2-(6-                                                                      n.sub.D.sup.22.5 1.5742                              chloro)pyridyloxy)propyloxy)-1-(3,3-dichloro-                                 2-propenyloxy)benzene                                                    (34) 3,5-Dichloro-4-(2-(N-phthalimido)ethoxy)-1-(3,3-                                                       m.p. 115.2° C.                                dichloro-2-propenyloxy)benzene                                           (35) 3,5-Dichloro-4-(3-(N-phthalimido)propyloxy)-1-                                                         m.p. 78.4° C.                                 (3,3-dichloro-2-propenyloxy)benzene                                      (36) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-                                                                n.sub.D.sup.20.5 1.5377                              pyridyloxy)propyloxy)-1-(3,3-dichloro-2-                                      propenyloxy)benzene                                                      (37) 3,5-Dichloro-4-(3-(3-chloro-5-trifluoromethyl-2-                                                       n.sub.D.sup.22.5 1.5429                              pyridyloxy)propyloxy)-1-(3,3-dichloro-2-                                      propenyloxy)benzene                                                      (38) 3,5-Dichloro-4-(3-(N-(1,2-dihydroxy-3-bromo-5-                                                         m.p. 119.5° C.                                trifluoromethyl-2-oxo)pyridyl)propyloxy)-1-                                   (3,3-dichloro-2-propenyloxy)benzene                                      (39) 3,5-Dichloro-4-(3-(2-benzimidazolylthio)pro-                                                           m.p. 120.7° C.                                pyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene                            (40) 3,5-Dichloro-4-(3-(2-benzothiazolyl-                                                                   n.sub.D.sup.22.5 1.6322                              thio)propyloxy)-1-(3,3-dichloro-2-propenyl-                                   oxy)benzene                                                              (41) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-                                                                m.p. 67.0° C.                                 pyridyloxy)ethoxy)-1-(3,3-dichloro-2-                                         propenyloxy)benzene                                                      (42) 3,5-Dichloro-4-(4-(5-trifluoromethyl-2-                                                                n.sub.D.sup.21.3 1.5359                              pyridyloxy)butyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (43) 3,5-Dichloro-4-(5-(5-trifluoromethyl-2-                                                                n.sub.D.sup.21.3 1.5307                              pyridyloxy)pentyloxy)-1-(3,3-dichloro-2-                                      propenyloxy)benzene                                                      (44) 3,5-Dichloro-4-(6-(5-trifluoromethyl-2-                                                                n.sub.D.sup.21.3 1.5302                              pyridyloxy)hexyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (45) 3-Chloro-5-methyl-4-(3-(5-trifluoromethyl-2-                                                           n.sub.D.sup.23.6 1.5294                              pyridyloxy)propyloxy)-1-(3,3-dichloro-2-                                      propenyloxy)benzene                                                      (46) 3-Chloro-5-methyl-4-(4-(5-trifluoromethyl-2-                                                           n.sub.D.sup.23.0 1.5275                              pyridyloxy)butyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (47) 3-Ethyl-5-methyl-4-(3-(5-trifluoromethyl-2-                                                            n.sub.D.sup.23.0 1.5188                              pyridyloxy)propyloxy)-1-(3,3-dichloro-2-                                      propenyloxy)benzene                                                      (48) 3-Ethyl-5-methyl-4-(4-(5-trifluoromethyl-2-                                                            n.sub.d.sup.23.0 1.5170                              pyridyloxy)butyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (49) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-                                                                n.sub.D.sup.25.0 1.5525                              pyridylamino)propyloxy)-1-(3,3-dichloro-2-                                    propenyloxy)benzene                                                      (50) 3,5-Diethyl-4-(3-(5-trifluoromethyl-2-                                                                 n.sub.D.sup.20.0 1.5192                              pyridylamino)propyloxy)-1-(3,3-dichloro-2-                                    propenyloxy)benzene                                                      (51) 3,5-Diethyl-4-(4-(5-trifluoromethyl-2-                                        pyridyloxy)butyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (52) 3,5-Dichloro-4-(4-(3-chloro-5-                                                trifluoromethyl-2-pyridyloxy)butyloxy)-                                       1-(3,3-dichloro-2-propenyloxy)benzene                                    (53) 3,5-Dichloro-4-(3-(3-bromo-5-                                                 trifluoromethyl-2-pyridyloxy)propyloxy)-1-                                    (3,3-dichloro-2-propenyloxy)benzene                                      (54) 3,5-Dichloro-4-(4-(3-bromo-5-                                                 trifluoromethyl-2-pyridyloxy)butyloxy)-                                       1-(3,3-dichloro-2-propenyloxy)benzene                                    (55) 3,5-Dichloro-4-(3-(3-fluoro-5-                                                trifluoromethyl-2-pyridyloxy)propyl-                                          oxy)-1-(3,3-dichloro-2-propenyloxy)benzene                               (56) 3,5-Dichloro-4-(4-(3-fluoro-5-                                                trifluoromethyl-2-pyridyloxy)butyloxy)-                                       1-(3,3-dichloro-2-propenyloxy)benzene                                    (57) 3,5-Dichloro-4-(3-(3,5-bistrifluoromethyl-2-                                  pyridyloxy)propyloxy)-1-(3,3-                                                 dichloro-2-propenyloxy)benzene                                           (58) 3,5-Dichloro-4-(4-(3,5-bistrifluoromethyl-2-                                  pyridyloxy)butyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (59) 3,5-Dibromo-4-(3-(5-trifluoromethyl-2-                                        pyridyloxy)propyloxy)-1-(3,3-dichloro-2-                                      propenyloxy)benzene                                                      (60) 3,5-Dibromo-4-(4-(5-trifluoromethyl-2-                                        pyridyloxy)butyloxy)-1-(3,3-dichloro-2-                                       propenyloxy)benzene                                                      (61) 3,5-Dichloro-4-(4-(5-trifluoromethyl-2-                                       pyridylamino)butyloxy)-1-(3,3-dichloro-2-                                     propenyloxy)benzene                                                      (62) 3,5-Diethyl-4-(3-(5-trifluoromethyl-2-                                        pyridylamino)propyloxy)-1-(3,3-dichloro-2-                                    propenyloxy)benzene                                                      (63) 3-Ethyl-5-methyl-4-(3-(5-trifluoromethyl-2-                                   pyridylamino)propyloxy)-1-(3,3-dichloro-2-                                    propenyloxy)benzene                                                      (64) 3-Chloro-5-methyl-4-(3-(5-trifluoromethyl-2-                                  pyridylamino)propyloxy)-1-(3,3-dichloro-2-                                    propenyloxy)benzene                                                      (65) 3,5-Diethyl-4-(4-(5-trifluoromethyl-2-                                        pyridylamino)butyloxy)-1-(3,3-dichloro-2-                                     propenyloxy)benzene                                                      (66) 3-Ethyl-5-methyl-4-(4-(5-trifluoromethyl-2-                                   pyridylamino)butyloxy)-1-(3,3-dichloro-2-                                     propenyloxy)benzene                                                      (67) 3-Chloro-5-methyl-4-(4-(5-trifluoromethyl-2-                                  pyridylamino)butyloxy)-1-(3,3-dichloro-2-                                     propenyloxy)benzene                                                      (68) 3,5-Dichloro-4-(2-(2-((2-(4-chlorophenyl)-                                    1,3-dioxanyl)))ethoxy)-1-(3,3-dichloro-2-                                     propenyloxy)benzene                                                      (69) 3,5-Dichloro-4-(2-(2-((2-(4-                                                  trifluoromethylphenyl)-1,3-dioxanyl)))ethoxy)-                                1-(3,3-dichloro-2-propenyloxy)benzene                                    (70) 3,5-Dichloro-4-(2-(2-((2-(4-                                                  trifluoromethoxyphenyl)-1,3-dioxanyl)))ethoxy)-                               1-(3,3-dichloro-2-propenyloxy)benzene                                    (71) 3,5-Dichloro-4-(3-(2-pyridyloxy)propylamino)-                                                          m.p. 76.2° C.                                 1-(3,3-dichloro-2-propenyloxy)benzene                                    ______________________________________                                    

The following are production examples for the intermediate compounds ofthe general formula [II] or [III].

Intermediate Production Example 1

A reaction vessel was charged with 5.0 g of 4-(benzyloxy)phenol and 100ml of carbon tetrachloride, to which a solution 5.43 g of t-butylhypochlorite dissolved in 5 ml of carbon tetrachloride was slowly addeddropwise, while stirring under ice cooling. After 24 hours, the reactionmixture was poured into water, followed by phase separation. The organiclayer (i.e., carbon tetrachloride layer) was washed with water, driedwith anhydrous magnesium sulfate, and concentrated to obtain a crudeproduct. The crude product was subjected to silica gel chromatography,which afforded 4.24 g of 2,4-dichloro-4-(benzyloxy)phenol (63% yield).

A reaction vessel was charged with 5.10 g of 1,3-dibromopropane, 2.40 gof potassium carbonate and 50 ml of N,N-dimethylformamide, to which asolution of 4.24 g of 2,6-dichloro-4-(benzyloxy)phenol dissolved in 10ml of N,N-dimethylformamide was slowly added dropwise. After stirring atroom temperature for 24 hours, the reaction mixture was poured intowater, and extracted twice with 150 ml of diethyl ether. The combinedether layer was washed with water, dried with anhydrous magnesiumsulfate, and concentrated to obtain a crude product. The crude productwas subjected to silica gel chromatography, which afforded 4.24 g of3,5-dichloro-4-(3-bromopropyloxy)-1(benzyloxy)benzene (68% yield).

A reaction vessel was charged with 4.24 g of3,5-dichloro-4-(3-bromopropyl-oxy)-1-(benzyloxy)benzene, 1.33 g ofbenzoic acid, 1.65 g of potassium carbonate and 20 ml ofN,N-dimethylformamide. After stirring at room temperature for 24 hours,the reaction mixture was poured into water, and extracted twice with 150ml of diethyl ether. The combined ether layer was washed with water,dried with anhydrous magnesium sulfate, and concentrated to obtain acrude product. The crude product was subjected to silica gelchromatography, which afforded 3.75 g of3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(benzoyloxy)benzene (80%yield).

A reaction vessel was charged with 3.75 g of3,5-dichloro-4-(3-benzoyloxypropy-loxy)-1-(benzyloxy)benzene, 5.0 g of10% aqueous potassium hydroxide solution and 50 ml of methanol. Afterstirring at room temperature for 24 hours, the reaction mixture wasconcentrated. The concentrate was poured into water, and extracted twicewith 150 m of diethyl ether. The combined ether layer was washed withwater, dried with anhydrous magnesium sulfate, and concentrated toobtain a crude product. The crude product was subjected to silica gelchromatography, which afforded 2.56 g of3-(2,6-dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol (90% yield).

A mixture of 0.5 g of 3-(2,6-dichloro-4-(benzyloxy)phenoxy)-1-propylalcohol thus obtained, 0.1 g of an oily mixture containing 60% sodiumhydride, and 3 ml of N,N-dimethylformamide was stirred at roomtemperature for 1 hour. Then, 0.3 g of2-chloro-5-trifluoromethylpyridine was added to this mixture, followedby heating to 100° C. After stirring continued for 1 hour, the mixturewas poured into 50 m of ice-water, and extracted with toluene at a totalvolume of 50 ml. The combined toluene layer was successively washed withdiluted hydrochloric acid and aqueous sodium bicarbonate solution, driedwith magnesium sulfate, and concentrated. The residue was silica gelchromatography, which afforded 0.5 g of1-benzyloxy-3,5-dichloro-4-[3-(5-trifluoromethylpyridin-2-yloxy)propyloxy]benzene(67% yield).

¹ H-NMR δ(ppm) [CDCl₃, TMS] 8.44 (1H, br, s), 7.76 (1H, dd), 7.2-7.5(5H), 6.90 (2H, s), 6.81 (1H, d), 5.00 (2H, s), 4.62 (2H, t), 4.11 (2H,t), 2.31 (2H, quint.).

A reaction vessel was charged with 0.5 g of1-benzyloxy-3,5-dichloro-4-(3-(5-trifluoromethylpyridin-2-yloxy)propyloxy)benzeneand 50 ml of ethyl acetate, and the air in the vessel was replaced withnitrogen. Then, 0.3 g of 10% palladium carbon was added, and thenitrogen in the vessel was replaced with hydrogen, followed by stirringat room temperature for 24 hours. The hydrogen in the vessel wasreplaced with nitrogen, after which the reaction mixture was filteredthrough Celite, and the filtrate was concentrated, which afforded 0.36 gof 3,5-dichloro-4-(3-(5-trifluoromethylpyridin-2-yloxy)propyloxy)phenol(92% yield).

¹ H-NMR δ(ppm) [CDCl₃, TMS] 8.45 (1H, br, s), 7.75 (1H, dd), 6.77 (2H,s), 6.75 (1H, d), 4.60 (2H, t), 4.15 (2H, t), 2.25 (2H, quint.) Thefollowing are specific examples of the intermediate compound of thegeneral formula [II] or [III] under the corresponding compound numbers.

1) 3,5-Dichloro-4-(6-chloro-3-pyridylmethyloxy)phenol

2) 3,5-Dichloro-4-(2,6-dichloro-3-pyridylmethyloxy)phenol

3) 3,5-Dichloro-4-(2-(1-pyrazolynyl)ethoxy)phenol

4) 3,5-Dichloro-4-(2-pyridylmethyloxy)phenol

5) 3,5-Dichloro-4-(2-thienylmethyloxy)phenol

6) 3,5-Dichloro-4-(2-furanylmethyloxy)phenol

7) 3,5-Dichloro-4-(3-pyridylmethyloxy)phenol

8) 3,5-Dichloro-4-(4-pyridylmethyloxy)phenol

9) 3,5-Dichloro-4-(2-(2-thienyl)ethoxy)phenol

10) 3,5-Dichloro-4-(2-(3-methylthiazol-2-yl)ethoxyphenol

11) 3,5-Dichloro-4-(2,4,5-trichloroimidazolynylmethyloxy)phenol

12) 3,5-Dichloro-4-(3,5-dimethyl-4-yloxazolynylmethyloxy)phenol

13) 3,5-Dichloro-4-(2-(3-thienyl)ethoxy)phenol

14) 3,5-Dichloro-4-(3-(4-pyridyl)propyloxy)phenol

15) 3,5-Dichloro-4-((2-(3,4-benzodioxanyl))methoxy)phenol

16) 3,5-Dichloro-4-((2,(5-formyl)furanyl)methoxy)phenol

17) 3,5-Dichloro-4-((3,(6-methylpyridyl)) methoxy)phenol

18) 3,5-Dichloro-4-(2-(4-pyridylthio)ethoxy)phenol

19) 3,5-Dichloro-4-(3-(3-pyridyl)propyloxy)phenol

20) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl nicotinate

21) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl isonicotinate

22) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl quinolinate

23) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 2-furanate

24) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 2-thiophenate

25) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 3-thiophenate

26) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl picolinate

27) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl quinolinate

28)3,5-Dichloro-4-(2-(2-((2-(4-chlorophenyl)-1,3-dioxanyl)))ethoxy)phenol

29) 3,5-Dichloro-4-(3-(2-pyridylthio)propyloxy)phenol

30) 3,5-Dichloro-4-(2-(6-ethoxy-2-benzothiazolyl)ethoxy)phenol

31) 3,5-Dichloro-4-(2-(2-benzoxazolyl)ethoxy)phenol

32) 3,5-Dichloro-4-(2-methyl-2-(2-(6-chloro)pyridyloxy)propyloxy)phenol

33) 3,5-Dichloro-4-(2-(N-phthalinirdo)ethoxy)phenol

34) 3,5-Dichloro-4-(3-(N-phthalimido)propyloxy)phenol

35) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

36)3,5-Dichloro-4-(3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)propyloxy)pheno

37) 3,5-Dichloro-4-(3-(N-(1,2-dihydroxy-3-bromo-5-trifluoromethyl-2oxo)pyridyl)propyloxy))phenol

38) 3,5-Dichloro-4-(3-(2-benzimnidazolylthio)propyloxy)phenol

39) 3,5-Dichloro-4-(3-(2-benzothiazolylthio)propyloxy)phenol

40) 3,5-Dichloro-4-(2-(5-trifluoromethyl-2-pyridyloxy)ethoxy)phenol

41) 3,5-Dichloro-4-(4-(5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

42) 3,5-Dichloro-4-(5-(5-trifluoromethyl-2-pyridyloxy)pentyloxy)phenol

43) 3,5-Dichloro-4-(6-(5-trifluoromethyl-2-pyridyloxy)hexyloxy)phenol

44)3-Chloro-5-methyl-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

45)3-Chloro-5-methyl-4-(4-(5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

46)3-Ethyl-5-methyl-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

47)3-Ethyl-5-methyl-4-(4-(5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

48)3,5-Dichloro-4-(3-(5-trifluoromethyl-2-pyridylamidno)propyloxy)phenol

49) 3,5-Diethyl-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

50) 3,5-Diethyl-4-(4-(5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

51)3,5-Dichloro-4-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

52)3,5-Dichloro-4-(3-(3-bromo-5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

53) 3,5-Dichloro-4-(4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

54)3,5-Dichloro-4-(3-(3-fluoro-5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

55)3,5-Dichloro-4-(4-(4-fluoro-5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

56) 3,5-Dichloro-4-(3-(3,5-bistrifluoromethyl-2-pyridyloxy)propyloxy)phenol

57)3,5-Dichloro-4-(4-(3,5-bistrifluoromethyl-2-pyridyloxy)butyloxy)phenol

58) 3,5-Dibromo-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)phenol

59) 3,5-Dibromo-4-(4-(5-trifluoromethyl-2-pyridyloxy)butyloxy)phenol

60) 3,5-Dichloro-4-(4-(5-trifluoromethyl-2-pyridylamino)butyloxy)phenol

61) 3,5-Diethyl-4-(3-(5-trifluoromethyl-2-pyridylamino)propyloxy)phenol

62)3-Ethyl-5-methyl-4-(3-(5-trifluoromethyl-2-pyridylamino)propyloxy)phenol

63) 3-Chloro-5-methyl-4-(3-(5-trifluoromethyl-2-pyridylamino)propyloxy)phenol

64) 3,5-Diethyl-4-(4-(5-trifluoromethyl-2-pyridylamino)butyloxy)phenol

65)3-Ethyl-5-methyl-4-(4-(5-trifluoromethyl-2-pyridylamino)butyloxy)phenol

66)3-Chloro-5-methyl-4-(4-(5-trifluoromethyl-2-pyridylamino)butyloxy)phenol

67)3,5-Dichloro-4-(2-(2-((2-(4-chlorophenyl)-1,3-dioxanyl)))ethoxy)phenol

68)3,5-Dichloro-4-(2-(2-((2-(4-trifluoromethylphenyl)-1,3-dioxanyl)))ethoxy)phenol

69)3,5-Dichloro-4-(2-(2-((2-(4-trifluoromethoxyphenyl)-1,3-dioxanyl)))ethoxy)phenol

The following are production examples for the intermediate compounds ofthe general formula [VII].

REFERENCE PRODUCTION EXAMPLE 1

A reaction vessel was charged with 30.5 g of 4-hydroxyphenyl benzoate,21.6 g of potassium carbonate, 20.8 g of 1,1,3-trichloropropene and 100ml of N,N-dimethylformamide. After stirring at room temperature for 15hours, the reaction mixture was poured into water, and extracted twicewith 50 ml of diethyl ether. The combined ether layer was washed withwater, dried with anhydrous magnesium sulfate, and concentrated toobtain a crude product. The crude product was subjected to silica gelchromatography, which afforded 44.1 g of4-(3,3-dichloro-2-propenyloxy)phenyl benzoate (96% yield).

A reaction vessel was charged with 44.1 g of4-(3,3-dichloro-2-propenyl-oxy)phenyl benzoate and 400 ml of methanol,to which 33 g of 30% potassium hydroxide solution was slowly addeddropwise under ice cooling. After stirring for 1 hour, the reactionmixture was made weakly acidic by the addition of 10% hydrochloric acid,and extracted twice with 150 ml of diethyl ether under salting out. Thecombined ether layer was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduct was subjected to silica gel chromatography, which afforded 26.0g of 4-(3,3-dichloro-2-propenyloxy)phenol (87% yield).

A reaction vessel was charged with 26.0 g of4-(3,3-dichloro-2-propenyloxy)phenol and 500 ml of carbon tetrachloride,to which a solution of 27.1 g of tert-butyl hypochlorite dissolved in 20ml of carbon tetrachloride was slowly added dropwise, while stirringunder ice cooling. After 24 hours, the reaction mixture was poured intowater, followed by phase separation. The organic layer (i.e., carbontetrachloride layer) was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduct was subjected to silica gel chromatography, which afforded 11.0g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol (32% yield),n_(D) ²².5 1.5895.

REFERENCE PRODUCTION EXAMPLE 2

A solution of 50 g of 4-bromo-6-chloro-2-methylphenol and 42.5 g ofbenzyl bromide dissolved in 200 ml of N,N-dimethylformamide was stirredat room temperature, to which 37.4 g of potassium carbonate was added,and the mixture was stirred for 12 hours. After completion of thereaction, the solvent was removed by distillation under reducedpressure, and the residue was added to 400 ml of diethyl ether, washedwith water, dried with anhydrous magnesium sulfate, and concentrated toobtain a crude product. The crude product was subjected to silica gelchromatography, which afforded 63 g of4-bromo-6-chloro-2-methyl-1-benzyloxybenzene (90% yield).

Then, 40 g of 4-bromo-6-chloro-2-methyl-1-benzyloxybenzene was dissolvedin 400 ml of tetrahydrofuran, followed by stirring at -70° C., to which76 ml of n-butyl lithium solution (in hexane, 1.69 mol/liter) was addeddropwise, followed by further stirring at -70° C. for 2 hours. To thisreaction mixture was added dropwise a solution of 13.3 g oftrimethoxyborane dissolved in 50 ml of tetrahydrofuran. Then, thereaction mixture was stirred for 1 hours, while warming to roomtemperature, and 100 ml of 10% aqueous hydrochloric acid solution wasadded in small portions, followed by stirring for 20 minutes. Thetetrahydrofuran layer was washed with water, dried with anhydrousmagnesium sulfate, and concentrated. The residue was mixed with 200 mlof toluene, and heated at 70° C. under stirring, to which 36 ml of 30%aqueous hydrogen peroxide solution was added dropwise. After heatingunder reflux for 1 hour, the reaction mixture was washed once withwater, twice with 10% ferrous sulfate and then ammonium water, and oncewith water, followed by phase separation. The toluene layer was driedwith anhydrous magnesium sulfate, and concentrated to obtain a crudeproduct. The crude product was subjected to silica gel chromatography,which afforded 29 g of 4-benzyloxy-3-chloro-5-methylphenol (91% yield).

To a solution of 27.3 g of 4-benzyloxy-3-chloro-5-methylphenol dissolvedin 250 ml of chloroform and being stirred at 0° C. were added 15.4 g ofbenzoyl chloride and then 13.3 g of triethylamine. After stirring atroom temperature for 2 hours, the chloroform layer was washed withwater, dried with anhydrous magnesium sulfate, and concentrated. Theresidue was subjected to silica gel chromatography, which afforded 35 gof 4-benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene (90% yield).

A reaction vessel was charged with 35 g of4-benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene and 200 ml of ethylacetate, and the air in the vessel was replaced with nitrogen. Then, 2 gof 10% palladium carbon was added, and the nitrogen in the vessel wasreplaced with hydrogen, followed by vigorous stirring at roomtemperature for 10 hours. The hydrogen in the vessel was replaced withnitrogen, after which the reaction mixture was filtered, and thefiltrate was concentrated. The residue was subjected to silica gelchromatography, which afforded 25 g of4-benzoyloxy-2-chloro-6-methylphenol (96% yield).

Then, 25 g of 4-benzoyloxy-2-chloro-6-methylphenol was dissolved in 250ml of chloroform, to which 12 g of chloromethyl methyl ether was added,while stirring at 0° C., and 21 g of N-ethyldiisopropylamine was addeddropwise. After heating under reflux for 1 hour, the chloroform layerwas washed with water, and concentrated. The residue was subjected tosilica gel chromatography, which afforded 27.4 g of3-chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene (96% yield).

Then, 26 g of 3-chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene wasdissolved in 200 ml of methanol, and the solution was stirred at roomtemperature for 1 hour, while adding dropwise 60 ml of 10% aqueouspotassium hydroxide solution. After completion of the reaction, thesolvent was removed by distillation under reduced pressure. The residuewas added to 150 ml of water, neutralized with 10% aqueous hydrochloricacid solution, and extracted with 200 ml of diethyl ether. The solventwas removed by distillation under reduced pressure, and the residue wassubjected to silica gel chromatography, which afforded 17.4 g of3-chloro-4-methoxymethoxy-5-methylphenol (96% yield).

To a mixture of 10 g of 3-chloro-4-methoxymethoxy-5-methylphenol, 7 g ofpotassium carbonate and 100 ml of N,N-dimethylformamide was addeddropwise a solution of 8 g of 1,1,3-trichloro-1-propene dissolved in 30ml of N,N-dimethylformamide, while stirring at room temperature. Afterstirring at room temperature for 12 hours, the reaction mixture waspoured into ice-water, and extracted twice with 200 ml of diethyl ether.The combined ether layer was washed with water, dried with anhydrousmagnesium sulfate, and concentrated. The residue was subjected to silicagel chromatography, which afforded 14.1 g of3-chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2propenyloxy)benzene(91% yield).

Then, 14.1 g of3-chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzenewas dissolved in 100 ml of 80% aqueous acetic acid solution, followed byheating under reflux with stirring for 1 hour. After completion of thereaction, the reaction mixture was mixed with 200 ml of water, andextracted twice with 200 ml of. diethyl ether. The combined ether layerwas washed with water, dried with anhydrous magnesium sulfate, andconcentrated. The residue was subjected to silica gel chromatography,which afforded 11.3 g of2-chloro-6-methyl-(3,3-dichloro-2-propenyloxy)phenol (93% yield), m.p.70.0° C.

The following is a production example for the intermediate compounds ofgeneral formula [XIII].

REFERENCE PRODUCTION EXAMPLE 3:

Production of3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

A reaction vessel was charged with 10.6 g of 1,3-dibromopropane, 5.53 gof potassium carbonate and 100 ml of N,N-dimethylformamide, to which asolution of 30.5 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoldissolved in 40 ml of N,N-dimethylformamide was slowly added dropwise.After stirring at room temperature for 24 hours, the reaction mixturewas poured into water, and extracted twice with 150 ml of diethyl ether.The combined ether layer was washed with water, dried with anhydrousmagnesium sulfate, and concentrated to obtain a crude product. The crudeproduct was subjected to silica gel chromatography, which afforded 11.1g of3,5-dichloro-4-(3bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene(77% yield), n_(D) ²⁴.0 1.5693.

The following are formulation examples in which "parts" are by weightand the present compounds are designated by the corresponding compoundnumbers as described above.

FORMULATION EXAMPLE 1:

Emulsifiable concentrates

Ten parts of each of the present compounds (1) to (70) are dissolved in35 parts of xylene and 35 parts of N,N-dimethylformamide, to which 14parts of polyoxyethylene styrylphenyl ether and 6 parts of calciumdodecylbenzenesulfonate are added, and the mixture is well stirred togive a 10% emulsifiable concentrate of each compound.

FORMULATION EXAMPLE 2:

Wettable powders

Twenty parts of each of the present compounds (1) to (70) are added to amixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrated silicon oxide fine powder and54 parts of diatomaceous earth, and the mixture is stirred with a mixerto give a 20% wettable powder of each compound.

FORMULATION EXAMPLE 3:

Granules

Five parts of each of the present compounds (I) to (70), 5 parts ofsynthetic hydrated silicon oxide fine powder, 5 parts of sodiumdodecylbenzenesulfonate, 30 parts of bentonite and 55 parts of clay aremixed, and the mixture is well stirred. Then, a suitable amount of wateris added to the mixture, which is further stirred, granulated with agranulator and then air-dried to give a 5% granule of each compound.

FORMULATION EXAMPLE 4:

Dusts

One part of each of the present compounds (1) to (70) is dissolved in asuitable amount of acetone, to which 5 parts of synthetic hydratedsilicon oxide fine powder, 0.3 part of PAP and 93.7 parts of clay areadded, and the mixture is stirred with a mixer. The removal of acetoneby evaporation gives a 1% dust of each compound.

FORMULATION EXAMPLE 5:

Flowables

Twenty parts of each of the present compounds (1) to (70) are mixed with1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solutioncontaining 2 parts of polyvinyl alcohol, and the mixture is pulverizedinto fine particles having a particle size of not more than 3 μm with asand grinder, to which 40 parts of an aqueous solution containing 0.05part of xanthan gum and 0.1 part of aluminum magnesium silicate areadded and then 10 parts of propylene glycol are added. The mixture isstirred to give a 20% water-based suspension of each compound.

FORMULATION EXAMPLE 6:

Oil solutions

First, 0.1 part of each of the present compounds (1) to (70) isdissolved in 5 parts of xylene and 5 parts of trichloroethane. Then, thesolution was mixed with 89.9 parts of deodorized kerosine to give a 0.1%oil solution of each compound.

FORMULATION EXAMPLE 7:

Oil-based aerosols

First, 0.1 part of each of the present compounds (1) to (70), 0.2 partof tetramethrin, 0.1 part of d-phenothrin, and 10 parts oftrichloroethane are dissolved in 59.6 parts of deodorized kerosine, andthe solution is put in an aerozol vessel. Then, the vessel is equippedwith a valve, through which 30 parts of a propellant (liquefiedpetroleum gas) are charged under increased pressure to give an oil-basedaerosol of each compound.

FORMULATION EXAMPLE 8:

Water-based aerosols

An aerosol vessel is filled with 50 parts of pure water and a mixture of0.2 part of each of the present compounds (1) to (70), 0.2 part ofd-allethrin, 0.2 part of d-phenothrin, 5 parts of xylene, 3.4 parts ofdeodorized kerosine and 1 part of an emulsifier [ATMOS 300 (registeredtrade name by Atlas Chemical Co.)]. Then, the vessel is equipped with avalve, through which 40 parts of a propellant (liquefied petroleum gas)are charged under pressure to give a water-based aerosol of eachcompound.

FORMULATION EXAMPLE 9:

Mosquito-coils

First, 0.3 g of each of the present compounds (1) to (70) is mixed with0.3 g of d-allethrin, and the mixture is dissolved in 20 ml of acetone.The solution is uniformly mixed with 99.4 g of a carrier formosquito-coils (prepared by mixing Tabu powder, pyrethrum marc powderand wood flour in the ratio of 4:3:3) under stirring. The mixture iswell kneaded with 120 ml of water, molded and dried to give amosquito-coil of each compound.

FORMULATION EXAMPLE 10:

Electric mosquito-mats

First, 0.4 g of each of the present compounds (1) to (70), 0.4 parts ofd-allethrin and 0.4 g of pipenyl butoxide are dissolved in acetone tohave a total volume of 10 ml. Then, 0.5 ml of the solution is uniformlyabsorbed in a substrate for electric mosquito-mats having a size of 2.5cm×1.5 cm×0.3 cm (prepared by forming a fibrillated mixture of cottonlinter and pulp into a sheet) to give an electric mosquito-mat of eachcompound.

FORMULATION EXAMPLE 11:

Heating smoke formulations

First, 100 mg of each of the present compounds (1) to (70) is dissolvedin a suitable amount of acetone. Then, the solution is absorbed in aporous ceramic plate having a size of 4.0 cm×4.0 cm×1.2 cm to give aheating smoke formulation of each compound.

FORMULATION EXAMPLE 12:

Poison baits

First, 10 mg of each of the present compounds (1) to (70) is dissolvedin 0.5 ml of acetone, and the solution is uniformly mixed with 5 g ofsolid bait powder for animals (Breeding Solid Feed Powder CE-2, tradename by Japan Clea Co., Ltd.). Then, the removal of acetone by airdrying gives a 0.5% poison bait of each compound.

The following test examples demonstrate that the present compounds areuseful as an active ingredient of insecticidal/acaricidal agents. Inthese test examples, the present compounds are designated by thecorresponding compound numbers as described above and the compounds usedfor comparison are designated by the corresponding compound symbols asshown in Table 47.

                                      TABLE 47                                    __________________________________________________________________________    Compound                                                                            Chemical structure         Remarks                                      __________________________________________________________________________    (A)                                                                                  ##STR96##                 Compound disclosed in JP-A                                                    48-86835/1973, page 23                       (B)                                                                                  ##STR97##                 Compound disclosed in JP-A 49-1526/1974,                                      page 22                                      __________________________________________________________________________

TEST EXAMPLE 1:

Insecticidal test against Spodoptera litura

A 200-fold dilution containing an active ingredient at 500 ppm, whichhad been prepared by diluting with water an emulsifiable concentrate ofthe test compound obtained according to Formulation Example 1, wasabsorbed at a volume of 2 ml in 13 g of an artificial diet forSpodoptera litura, which had been prepared in a polyethylene cup havinga diameter of 11 cm. Ten fourth-instar larvae of Spodoptera litura wereset free in the cup. After 6 days, the survival of larvae was examinedto determine the mortality. The test was conducted in duplicate.

As a result, it was found that the present compounds (1), (2), (5)-(7),(9)-(11), (14), (16)-(18), (20)-(26), (28)-(37) and (39)-(50) exhibitedthe mortality of 80% or more. In contrast, both compounds (A) and (B)for comparison exhibited the mortality of 0%.

TEST EXAMPLE 2:

Test against Tetranychus urticae Koch

Ten female adults of Tetranychus urticae Koch per one leaf were allowedto parasitize to a potting bean at the primary leaf stage harvested for7 days after seeding, and these pots were placed in a thermostated roomat 25° C. After 6 days, a chemical solution containing an activeingredient at 500 ppm, which had been prepared by diluting with water anemulsifiable concentrate of the test compound obtained according toFormulation Example 1, was sprayed at a volume of 15 ml over each pot ona turntable. At the same time, 2 ml of the same solution was drenched inthe soil. After 8 days, the degree of damage on the respective plantscaused by Tetranychus urticae Koch was examined. The effects weredetermined according to the following criteria:

-: Damage is scarcely observed.

+: Damage is slightly observed.

++: Damage is observed at the same level as in the non-treated field.

As a result, it was found that the present compounds (1), (7), (10),(15), (30), (32) and (33) were evaluated as "-" or "+". In the contrast,both compounds A and B for comparison were evaluated as "++".

TEST EXAMPLE 3:

Insecticidal test against Heliothis virescens

A dilution containing an active ingredient at 100 ppm, which had beenprepared by diluting with water an emulsifiable concentrate of the testcompound obtained according to Formulation Example 1, was incorporatedat a volume of 0.2 ml in an 25 artificial diet. A second-instar larva ofH. virescens was given the diet and bred in a plastic vessel. Teninsects were used by each treatment. After 6 days, the mortality wasdetermined.

As a result, it was found that the present compounds (36), (42) and (43)exhibited the mortality of 80% or more. In contrast, both compounds (A)and (B) for comparison exhibited the mortality of 0%.

TEST EXAMPLE 4:

Insecticidal test against Plutella xylostella

A chemical solution containing an active ingredient at 50 ppm, which hadbeen prepared by diluting an emulsifiable concentrate of the testcompound obtained according to Formulation Example 1 with watercontaining spreading agent RINOU (Nihon Nouyaku K.K.) to a degree suchthat the spreading agent had been 1000-fold diluted, was sprayed at avolume 25 ml over each pot of a potting cabbage at the five leaf stage.The treated plants were air dried, on which ten third-instar larvae ofPlutella xylostella were set free. After 4 days, the mortality wasdetermined.

As a result, it was found that the present compounds (36), (37), (42)and (45)-(48) exhibited the mortality of 80% or more. In contrast, bothcompounds (A) and (B) for comparison exhibited the mortality of 0%.

Industrial Applicability

The present compounds have excellent insecticidal/acaricidal activity,so that they are satisfactorily effective for the control of noxiousinsects, mites and ticks.

We claim:
 1. A dihalopropene compound of the general formula: ##STR98##wherein Z is oxygen, sulfur or NR⁴ (wherein R⁴ is hydrogen or C₁ -C₃alkyl); Y is oxygen, sulfur or NH; X's are independently chlorine orbromine; R², R³ and R¹⁰ are independently halogen, C₁ -C₃ haloalkyl orC₁ -C₃ alkyl; t is an integer of 0 to 2; and R¹ is Q₁, Q₂, Q₃, Q₄, Q₅,Q₆ or Q₇ of the general formula: ##STR99## wherein A is an optionallysubstituted 5- or 6-membered heterocyclic ring group with only oxygen orsulfur heteroatoms in addition to carbon atoms, provided that when A isan optionally substituted heterocyclic ring group containing two oxygenatoms and a condensed benzene ring, A is optionally substituted1,3-benzodioxolan-2-yl or optionally substituted 1,4benzodioxan-2-yl; Bis oxygen, S(O)_(q), NR⁹, C(=G¹)G² or G¹ C(=G²); q is an integer of 0 to2; R⁹ is hydrogen, acetyl or C₁ -C₃ alkyl; G¹ and G² are independentlyoxygen or sulfur; R⁵, R⁶, R⁷, R¹¹ and R¹² are independently hydrogen, C₁-C₃ alkyl or trifluoromethyl; R¹³ and R¹⁴ are independently hydrogen, C₁-C₃ alkyl, trifluoromethyl or halogen; p is an integer of 0 to 6; and sis an integer of 1 to
 6. 2. The dihalopropene compound according toclaim 1, wherein A is a 5- or 6-membered heterocyclic ring groupcontaining at least one oxygen or sulfur atom and optionally substitutedwith (R⁸)_(r), wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂haloalkylsulfinyl, C₁ -C₂ haloalkylsufonyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino,acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -C₆cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl or (di(C₁ -C₂alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy, benzyloxy orpyridyloxy, each of which is optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and r is aninteger of 0 to
 7. 3. The dihalopropene compound according to claim 1,wherein A is 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 1,3-dioxolanylor 1,4-benzodioxanyl, each of which is optionally substituted with(R⁸)_(r), wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino,acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -Clcycloalkyl, (C₁ -C₂ alkyl)-aminocarbonyl or (di(C₁ -C₂alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy, benzyloxy orpyridyloxy, each of which is optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and r is aninteger of 0 to
 7. 4. The dihalopropene compound according to claim 1,wherein R² and R³ are independently halogen or C₁ -C₃ alkyl; and t is 0.5. The dihalopropene compound according to claim 1, wherein R² and R³are independently chlorine, bromine, methyl, ethyl or isopropyl; and tis
 0. 6. The dihalopropene compound according to claim 1, wherein R² andR³ are both chlorine; and t is
 0. 7. The dihalopropene compoundaccording to claim 1, wherein R² is chlorine; R³ is methyl; and t is 0.8. The dihalopropene compound according to claim 1, wherein R² is ethyl;R³ is methyl; and t is
 0. 9. The dihalopropene compound according toclaim 1, wherein R² and R³ are both bromine; and t is
 0. 10. Thedihalopropene compound according to claim 1, wherein R² and R³ are bothethyl; and t is
 0. 11. The dihalopropene compound according to claim 1,wherein R² and R³ are independently halogen or C₁ -C₃ alkyl; t is 1 or2; and R¹⁰ is halogen or C₁ -C₃ alkyl.
 12. The dihalopropene compoundaccording to claim 1, wherein R² and R³ are independently halogen or C₁-C₃ alkyl; t is 1 or 2; and R¹⁰ is halogen.
 13. The dihalopropenecompound according to claim 1, wherein Y and Z are both oxygen.
 14. Thedihalopropene compound according to claim 4, wherein Y and Z are bothoxygen.
 15. The dihalopropene compound according to claim 1, wherein R¹is Q₁.
 16. The dihalopropene compound according to claim 1, wherein R¹is Q₁ ; p is 1 to 6; and A is 2-thienyl, 3-thienyl, 2-furanyl, 3-furanylor 1,3-dioxolanyl, each of which is optionally substituted with(R⁸)_(r), wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino,acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -C₆cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl or (di(C₁ -C₂alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy, benxyloxy orpyridyloxy, each of which is optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and r is aninteger of 0 to
 7. 17. The dihalopropene compound according to claim 14,wherein R¹ is Q₁ ; p is 1 to 6; and A is 2-thienyl, 3-thienyl,2-furanyl, 3-furanyl or 1,3-dioxolanyl, each of which is optionallysubstituted with (R⁸)_(r), wherein R⁸ is halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃alkylthio, C₁ -C₃ haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂alkylsulfonyl, C₁ -C₂ haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂-C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl,amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl,methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl or(di(C₁ -C₂ alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy,benzyloxy or pyridyloxy, each of which is optionally substituted withhalogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃haloalkoxy; and r is an integer of 0 to
 7. 18. The dihalopropenecompound according to claim 14, wherein R¹ is Q₁ ; p is 1 to 6; R⁵, R⁶and R⁷ are all hydrogen; and A is 1,3-dioxolanyl optionally substitutedwith (R⁸)_(r), wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃haloalkylthio, C₁ -C₂ alkyl-sulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino,acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -C₆cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl or (di(C₁ -C₂alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy, benzyloxy orpyridyloxy, each of which is optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and, r isan integer of 0 to
 5. 19. The dihalopropene compound according to claim14, wherein R¹ is Q₁ ; p is 1 to 4; R⁵, R⁶ and R⁷ are all hydrogen; andA is 1,3-dioxolanyl optionally substituted with (R⁸)_(r), wherein R⁸ ishalogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁-C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₁ -C₂alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂ haloalkylsulfonyl, C₂ -C₄alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl, amino,dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl,methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl or(di(C₁ -C₂ alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy,benzyloxy or pyridyloxy, each of which is optionally substituted withhalogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃haloalkoxy; and r is an integer of 0 to
 5. 20. The dihalopropenecompound according to claim 1, wherein R¹ is Q₁ ; p is 0; and A is-2thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 1,3-dioxolanyl or1,4-benzodioxolanyl, each of which is optionally substituted with(R⁸)_(r), wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃haloalkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂haloalkylsulfinyl, C₁ -C₂ haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino,acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -C₆cycloalkyl, (C₁ -C₂ alkyl)aminocarbonyl or (di(C₁ -C₂alkyl)amino)carbonyl, or R⁸ is phenyl, benzyl, phenoxy, benzyloxy orpyridyloxy, each of which is optionally substituted with halogen, C₁ -C₄alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₃ haloalkoxy; and r is aninteger of 0 to
 7. 21. The dihalopropene compound according to claim 1,wherein R¹ is Q₂.
 22. The dihalopropene compound according to claim 1,wherein R¹ is Q₂ ; and A is 2-thienyl, -3thienyl, 2-furanyl or3-furanyl, each of which is optionally substituted with (R⁸)_(r),wherein R⁸ is halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁-C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio,C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂ haloalkylsulfinyl, C₁-C₂ haloalkylsulfonyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄alkynyl, C₂ -C₄ haloalkynyl, amino, dimethylamino, acetamido, acetyl,haloacetyl, formyl, carboxyl, methoxycarbonyl, C₃ -C₆ cycloalkyl, (C₁-C₂ alkyl)aminocarbonyl or (di(C₁ -C₂ alkyl)amino)carbonyl, or R⁸ isphenyl, benzyl, phenoxy, benzyloxy or pyridyloxy, each of which isoptionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁-C₄ alkoxy or C₁ -C₃ haloalkoxy; and r is an integer of 0 to
 7. 23. Thedihalopropene compound according to claim 14, wherein R¹ is Q₃.
 24. Thedihalopropene compound according to claim 14, wherein R¹ is Q₄.
 25. Thedihalopropene compound according to claim 14, wherein R¹ is Q₅.
 26. Thedihalopropene compound according to claim 14, wherein R¹ is Q₆.
 27. Thedihalopropene compound according to claim 14, wherein R¹ is Q₇. 28.Compound of claim 1 being3,5-Dichloro-4-(2-(2-(4-chlorophenyl)-1,3-dioxolan-4yl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene.29. An insecticidal/acaricidal agent comprising the dihalopropenecompound according to claim 1 as an active ingredient.
 30. A phenolcompound which is3,5-dichloro-4-(2-(2-(4-chlorophenyl)-1,3-dioxolan-4-yl)ethoxy)phenol.